


Don't Knock It Until You Try It

by Silent_Chick



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Modern Setting, Bakery Shop Owner Dean Winchester, Birth Control, Blow Jobs, Bookstore Owner Reader, Come Swallowing, F/M, Friends to Lovers, Oral Sex, Original Character(s), Original Female Character(s) - Freeform, Penis In Vagina Sex, Plot What Plot/Porn Without Plot, Public Sex, Reader Receives Head, Reader-Insert, Semi-Public Sex, Sex Talk, Smut, Tags Are Hard, Vaginal Fingering, Vaginal Sex, no protection, shop owners
Language: English
Status: Completed
Published: 2017-01-25
Updated: 2017-12-12
Packaged: 2018-09-19 20:01:52
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 16
Words: 24,754
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9458348
Author URL: https://archiveofourown.org/users/Silent_Chick/pseuds/Silent_Chick
Summary: Dean proves the reader wrong, when it comes to the real thing.[JUST SMUT]





	1. Chapter 1

Shutting off the lights in his bakery, Dean grabs the little box on the counter along with the plastic fork he put beside it. He takes the keys from his pocket and locks up the front door.

Taking a few steps to the right, brings him in front of a book store. Dean opens the door, closing it behind himself.

"Hey." Dean calls out to the woman at the waist high counter.

"Hey, Dean. Good day at the bakery?" The store owner asks, placing her thumb in the book she was reading.

"Yeah, got some new costumers. I brought you your pie."

Dean comes around the counter, placing the box down and gives her a hug.

"Yes. Always the best part my day."

Dean chuckles, sliding off his jacket and puts it in the chair behind her.

"Seein' me isn't the best part."

(Y/N) looks at him with the fork in her mouth. "No, it's an addition."

"Addition?" Dean leans on the counter beside a pile of books.

"Mhmm. Best part, great pie. Addition, eye candy, that cooked said pie."

"Ah, I get it now. You only keep around for free dessert."

(Y/N) shakes her head pausing her eating to look at him. "That's not true. I keep you around so you can pick things up for me with your big manly arms. Like that box over there."

Dean smiles at her as she tries to look innocent.

"So, I'm your bitch."

"...My manly bitch."

Dean laughs, coming from behind the counter. He heads towards the box filled with books to bring to the back.

They met a few years ago. (Y/N) was already here with her shop and Dean moved into the open one next to her, starting his bakery.

She came over with a book, giving it to him as a welcome gift. Dean began speaking with her and of course he started flirting, only to reveal that she had a boyfriend at that time. It was bad news for Dean because even though he just moved in next door, he was going to ask her out, eventually.

In a few months of him being here, they formed a close friendship. So close, that one day, (Y/N) came over on her lunch break and made her way around his display of desserts just to bury her head in his chest.

He wrapped his arms around her, having noticed she didn't say anything when she entered. Dean asked her what was wrong and she pulled back with a grim expression telling him her boyfriend broke up with her the day before.

Dean went to the door and flipped his out for lunch sign around and escorted her to the kitchen. They sat and shared a pie. That's how his daily free dessert became a thing. He'd come over and keep her company, since he always closes the shop two hours before her.

And by this time Dean accepted she wasn't interested in him or so he thought. One day, well away from the break up, he came over to the book store with his free dessert. They exchanged greetings and she asked him to put some books on the shelves. He started putting his self to use and the whole time he felt like he was being watched. Turning his head, he made eye contact with her as she ate her cheesecake slice.

He jokingly asked "if she saw something she liked" and in return she, half-jokingly/ half-seriously said, "you".

Dean didn't know what to do so he just went the safe route and chuckled, getting back to what he was doing.

They've been flirting ever since.

Recently, it's gotten heavier. They have each other's numbers, so sometimes she'll send him things that she saw in a romance novel she was reading. That's mainly what she likes to read. But the inserts would always have something to do with something sexual.

It didn't matter the time of day or anything.

He came back from setting the box down on a table in the back. She picked up the book she was reading when he walked in and eats her pie at the same time.

Dean was playing a game on his phone when he heard her teeth kiss.

"Disappointed again?" He asks, not removing his eyes from his phone.

"No... I just wish they would make sex scenes more realistic in the book. I get it's supposed to be fiction but come on."

"Is it not still good though?"

She places a bookmark in the page and sets it to the side. "It's okay, but it's making it seem like sex in public is the best thing ever."

Dean's brow lifts and he sets his distraction to the side. "Is it not?"

"I wouldn't know because I've never been in that situation. Do you think public sex is amazing as this book is trying to tell me it is?"

Dean turns to face more towards her. "I don't know what the book is saying."

"I just find it kind of annoying how every time I read something and they have sex in public the woman has on a dress or a skirt. Like just be real for a second put her in some damn shorts at least. Oh, and let me not forget, they always seem to have a thong on. And then it's always in some park, like really?"

"You can't really knock it if you haven't tried it." Dean reasons, licking his dry lips.

"And you have?" She questions, changing her own position.

"A few times."

"How did that turn out?"

"Great, I guess. Don't really have worry about pickin' up clothes. Havin' sex outside is kind of liberating, not just outside but like in a library or something."

(Y/N)'s brows lifts. "You had sex in a library?"

Dean looks her up and down stopping for two seconds on her breast. He can slightly see both of her nipples poking through whatever bra she has on and her red t-shirt.

"Yeah, dated a chick that worked there."

"Oh." She says, clearing her throat.

Dean gets a little closer to her, leaning his forearms on the counter. "Would you ever consider havin' sex in public?"

(Y/N) takes a deep breath, seeming to really think about the question.

"Yes, if it's with someone I trust. I could see myself doing it. I don't know if I could do it in a library though." She laughs.

"What about a book store?"

(Y/N) drops the empty pie box she was tossing in the trash. She picks it up and turns to see Dean curiously gazing at her, waiting for her answer.

"Ma-maybe. Sure."

Two costumers walk in and she greets them, letting them know if they need anything just ask. (Y/N) was watching, just in case they waved her over, when Dean made his way behind her. He pressed his body against her and heard her gasp.

"Relax." He whispers.

Dean squeezes her waist while his other hand goes to the front of her jeans, popping the button and slowly sliding down the zipper.

(Y/N)'s hands ball up on the counter. Dean places a kiss on her neck, keeping his eyes on the other women in the store. The hand that was on her waist goes to her breast squeezing and teasing them through her shirt.

He feels her push her ass against his crotch. His cock twitches with interest. Slyly, Dean grabs her panties and jeans and slowly pulls them down as he crouches behind her.

Dean comes back up with a hand inserted between her thighs. (Y/N) takes off her shoes and quietly maneuvers herself out of her clothes, spreading her legs, leaning forward on the counter.

Removing the hand, Dean licks his fingers just to return it in between her folds. He slowly begins to rub and she slowly moves her hips in circles.

Dean proceeds to undo his buckle, making sure it doesn't make too much noise. Pants undone, he pulls them down under his ass along with his underwear. Licking his hand, he strokes himself.

(Y/N) looks at him then at the cock in his hand, biting her lip.

Dean stops rubbing her and goes down behind the counter, between her legs. The first flick of his tongue gets him a shudder. He has her bend her knees a bit and starts to suck at her clit.

A hand shoots down to the top of his head gripping his hair.

"Need anything else today?" (Y/N) asks politely, bringing her hand up as if she was just placing something on the ground.

"No, that's it. Thanks."

Dean shoves his tongue into her pussy, swiping his thumb across the red tip of his dick.

"Ah-lright, that will be $5.49."

Money exchange hands and she straightens up to open the register. Dean shoves two fingers in alongside his tongue.

Her thighs shake a little and she clears her throat.

"Your change and receipt. Have a nice day and make sure to come back sometime." She says, once she bagged the book.

"Oh, I will. Have a good one."

"You too."

The shop door closes and she grinds on Dean's face. Her breathing is heavy, when Dean comes back up off the ground.

"Lean forward." He tells her, spreading her legs.

Dean gives his cock two more strokes before he shoves it in her pussy.

The action caught her off guard and she brought her hand back and smacked his hip, literally at a loss for words.

Dean starts with long deep strokes, squeezing her titties and keeping an eye out the front window of the shop.

Around this time people usually aren't around here because most of the shops close early. So, they should be good.

"Oh fuck... don't stop, please don't stop."

(Y/N)'s holding onto the edge of the counter. Dean moves his hands to her hips, she's on her tip toes at this point. Keeping her from moving back on him, he draws his cock out pounding back in. Her breath catches in her throat. Her whines for him to keep going egg him on along with the sound of skin on skin.

His last thrust leaves her in a shaking mess. Her hips jolt forward unintentionally as her legs shake. She's still quietly whining as he looks around for something to release his release in. (Y/N) looks at him and drops to her knees, taking his cock in hand. She begins sucking at the tip, stroking the rest.

Dean rests his hand on her head. Feeling her tongue go across his slit, he releases a groan as he feels himself shoot cum into her mouth.

(Y/N) licks the tip, cleaning it up when Dean draws her up. He captures her lips, hands gripping her ass. He's still hard and (Y/N) instantly realizes this. She throws his jacket out the chair and has him sit.

She puts his dick back inside her, holding onto the counter. (Y/N) bounces up and down on his cock, enjoying every second of it. Dean takes her hips and slams her back down onto himself.

"I should've let you fuck me sooner." She says when Dean was drawing out again.

Back down on him, she grinds against him with his cock inside.

"I'm 'bout to cum." Dean tells her fingers having tightened on her hips.

"Go ahead." She tells him.

"What?"

"I'm on birth control. Just fuck me." She raises herself back up and slams down.

A few more deep thrusts, Dean's arm goes around her waist and he glues himself to her back as they both orgasm once again.

He removes his arm, and groans at the cum that comes out of her. She turns around and places herself back on his lap above his spent dick and kisses him. While his tongue is her mouth he takes advantage of the ass in his reach. She moans, pulling back with a hand in his hair.

"Was that realistic enough for you?" He asks, hands resting on her ass.

"It still kind of feels like a fantasy."

"I'll take that as a compliment."

They get cleaned up after that and while they wait for the shop to close, Dean sits in the chair and has her sit down in his lap and read to him. When she closes up the shop and the lights go out, Dean traps her against one of the shelves and drops to his knees again.

Before they left her shop for the night, she did declare that was the best sex she ever had.

Moral of the story: Don't knock it until you try it.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	2. Chapter 2

Dean came into the bookstore walking around the shelves. (Y/N) had him and his brother move them into a slanted position, so if you’re looking into the window you would see all the books instead of seeing down the aisle and straight to the cash register. 

“Hey Babe.” He greets with a kiss after he finds her with a clipboard in her hand. 

“Hey.” 

“You look nice.” Dean takes her hand and spins her around, taking in the view. 

She had on a black waist high skirt that stopped at mid-thigh and a spaghetti strap purple flowy shirt. He saw her earlier, but the shop was so busy all he had time to do was kiss her and give her a muffin and the drink she wanted. He didn’t even take a lunch break. 

“Thank you. I’m just taking inventory.” (Y/N) tells him. 

Dean nods and heads behind the counter to the seat behind it. He places his jacket on the back of it and sits. With nothing else to do, he sets his head down on his arms and quietly watches as she does her job. 

He notices that there is no other strap other than the ones on her shirt. But that’s fine a lot of women don’t wear bras with those kinds of shirts. 

(Y/N) was twirling her pen by her side and ended up dropping it. Instead of crouching down with her knees together like most women do, she backs up, spreads her legs apart, and bends down. 

Dean’s head turns to the side automatically, like a dog picking up on a noise. 

He reasoned for the missing bra, but the panties… The panties are just nonexistent. 

She stays down longer than she has to, before she comes back up. 

Well he be damned, if he says anything to ruin the show he must have before him. 

Dean slouches a bit in the chair, waiting for her next move. He gently rubs his cock through his jeans. 

(Y/N) marks another thing down on her clipboard. 

He hears something hit the floor and looks down to see that his phone fell out of his pocket. Picking it up, he turns it about to make sure no damage was done and throws it on the counter in front of him. When he looks back up, it’s to (Y/N) having turned around and the top of her shirt is hanging down. 

She looks indifferent, focusing on her clipboard. 

Somehow her tits jiggle with each movement of her pen. 

Dean frees himself from his pants, licks his hand, and begins to slowly pump his cock. 

“Dean?” 

“Mhm?” 

“Can you count how many of these blue books I have up here?” 

Dean looks down at his dick and back at her. “Yeah.” 

Cock standing proud, he makes his way around towards her. When he makes it over she points out the books she was talking about. Dean begins counting and (Y/N) traps his free arm in between hers. Feeling the bottom of the skirt on his fingertips, he moves his hand back until it’s against her pussy and lightly teases her clit. 

When he really begins counting, he feels her hand close around his cock and pump the way he was before. 

“Nine.” He supplies, fucking into her hand. 

She squeezes his cock and presses her thumb down on his slit, before taking her hand away and removing herself from him. 

“Thank you.” 

“No problem.” 

Biting his lip, he returns to the chair. A little bit after she comes around. Putting the clipboard down she sorts through some papers. (Y/N) has them in her hand when she backs her ass on top of his dick. She looks through the papers and when she moves forward again, Dean takes his cock and moves it so it’ll rub against her pussy instead. 

He hears her take in a breath. 

(Y/N) clips a few of the papers on her clipboard and begins to straighten up. 

Not able to stay quiet anymore, Dean pins her against him with an arm around her waist. 

“I have to finish, Dean.” She tells him, holding onto his arm. 

“Yeah? You really wanna finish or do you wanna take this dick?” He whispers, kissing across her shoulders. 

(Y/N) slowly gets up and turns around, looking at his cock. “Take your dick.” 

Dean springs forward, bends her over the counter, and thrusts in. Taking her hands, he holds them above her head. He slaps and squeezes her ass, having lifted the skirt onto her back. 

As he pounds in, (Y/N) makes uncoherent noises. Removing his hand from her hands, Dean places it around her neck, squeezing only slightly. Pure ecstasy covers her face as her eyes are barely closed and her mouth hangs open. 

“You wanna finish now?” Dean asks with an authoritative tone. 

“No.” She cries. 

“No what?” He demands, smacking her ass. 

“No, Sir.” 

“That’s what I thought.” 

Dean was going to let her plant her feet on the ground, so he could get a new angle. But her legs wouldn’t allow it. Manhandling her off the counter, he picks her up, cock trapped in between her pussy and his stomach. 

He makes his way to the very back of the store, sucking on her nipples. When he doesn’t see any clear room on one of the tables, he swipes his arm across it, knocking all of the books off. 

Laying her down on her back on the table, he drags her forward so her ass hangs off. 

Directing his dick back in, he picks up where he left off. Dean puts his hand back on her neck, squeezing as he did once before. (Y/N) grips his arm with both of her hands, back arching off the table. 

The table creaks along with Dean’s fast pace. 

“Oh God… Oh my God… Dean…”

Tightening his hand just a tad, her back arches one final time and her eyes roll back. Feeling her constrict around him has him cumming harder than he has in a while. He thrusts out his final ropes of cum, before slowly pulling out. 

They both are breathing hard. Dean fixes his clothes and raises her up with a hand on the back of her neck. Dean sweetly kisses her, before he puts her arms through her shirt straps. 

“You okay?” He asks, swiping his thumb across her cheek. 

“Yeah. That went better than I thought it would.” 

Dean chuckles. “Two birds with one stone.” 

“I thought you forgot about the text I sent earlier.” (Y/N) grabs his hand, rubbing her thumb back and forth. 

“If anybody is gonna choke you, I’d rather it be me.” 

(Y/N) gets off the table, holding her skirt up to avoid the cum on her. “If I asked you to do more than choke me, would you?” 

“Depends on what it is.” He answers honestly. 

She nods and makes her way into the bathroom. Dean leans on the doorframe outside of it, staring at the floor. 

“What would you want me to do?” 

“Um, it wouldn’t be anything that causes damage.” 

“As long as I’m not hurtin’ you, I’m fine with it.” 

The toilet flushes and the sink turns on. Once she comes out, (Y/N) kisses him again. 

“I’m happy to hear that. Now, pick up my books.” She begins to walk past him and he grabs her hand. 

“Could you ask me nicely?” 

(Y/N) comes back, placing a hand on his chest. “Could you please pick up the books you swiped on the floor when you were fucking my brains out, my manly bitch?” 

Dean bursts out laughing, nodding. 

He starts picking up the books, placing them neatly back on the table top. 

“Dean?” 

He turns his head and she has her tit in her hand. She knows how much he loves them. 

“You better get out of here before you start somethin’ else.” Dean tells her, completely serious. 

“How do you know I’m not trying to?” 

“Because my dick gotta get a minute to recuperate.” 

It’s her turn to laugh as she walks out of the back room. 

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	3. Chapter 3

(Y/N) bought panties. Not just any panties. Vibrating panties.

The only reason Dean knows this is because when he knocked on her door, so they could go shopping together, she placed a remote in his hand and told him what it was for.

She didn't say whether she had them on or not, but he assumes she does since he currently has the remote in his pocket.

(Y/N) told him that he had all control. Not to tell her when he was going to do it, how long, and he could activate it anywhere. He asked if she tried it out to make sure it worked, the reply he got was, "not with them on". So, she has no idea how strong the vibration could be...

This should be fun.

They were shopping for new paintings to put in Dean's shop. But really it was like a date because they are going out to eat after they find a few things.

It would be their first date-ish thing since kind of being together. They haven't actually talked about anything. Dean treats her the same as if they were exclusively seeing each other. And hopefully she is also.

They couldn't be friends with benefits. You don't have the sex they have with a FWB that's some reserved red carpet shit.

There has been no titles to get thrown around, frankly Dean hasn't thought about it. But what if he sees a friend or family member of his, then what does he introduce her as? If she's not on board with the girlfriend thing, then he'll have to say friend and then people will think they're FWB's and that's not what Dean wants.

"Dean?"

"Hm?" He asks looking down at her where they stopped in front of some decorations.

"Doing okay? You spaced out."

"Yeah, just thinkin' about what I want to get."

(Y/N) picks up a little glass panda with shades. "What do you think?"

"I think it'll fit in at the book store." He says slyly going into his pocket.

She about jumps a foot in the air with the panda gripped tightly. (Y/N) begins laughing, looking down the rest of the aisle.

Dean switches it to medium. Neither say anything as she stands with a hand on over her mouth looking at the other little glass animals.

Dean wraps his arm around her dragging her closer. When she gets against him, she crosses her legs at the ankles, resting her head on his arm.

He switches it back to high.

"Fuck..." (Y/N) whispers with her eyes closed.

"Talk to me, Baby. How ya feelin'?" He pats her hip.

"I feel like I want you to fuck me right now." She answers truthfully. (Y/N) untucks herself from his arm, fanning her face with her free hand. "I didn't think it would be this good."

Dean turns it off.

"Whew, um, shit. Maybe I should’ve tried it at home first.”

The only reason Dean turned it up that high was because they were in the aisle alone. The vibrator can definitely be heard that high.

She's still fanning her face.

"Let's go look at some other stuff." Dean places his hands on their basket.

They venture through other parts of the store, until they finally get where they’re supposed to be. Dean decides to get a painting with some autumn trees, one that has different tones of blue on it, a colorful one of a city, and a colorful world map.

When he was putting the last one in the basket, (Y/N) ventured off somewhere; so, Dean ventured towards the chips again.

He was staring at the selection before him, when his phone started ringing.

“I’m in the chip aisle.”

(Y/N) clears her throat, “could you come to the women’s clothing section? My ex is here and he’s coming towards me as we speak.” She says quietly into the phone.

“Yeah, here I come.”

“Thanks. Hey Jason, how’ve you been?” She hangs up after her cheery greeting.

When Dean spots her, he switches the remote in his pocket to low. (Y/N) shifted her feet, fiddling with the sweaters they were standing by.

“Yeah, no, the shop is great. Doing real good. How’s-how’s your job going?” She was saying as he came up behind her.

“Well I quit working at the call center and became a firefighter. The work schedule is crazy but I love it, makes me good money.”

Jason is a good three inches shorter than Dean. He’s a brunette and he has light brown eyes. To let her know he’s behind her, Dean lightly hits her butt with the basket and it causes her to look back.

She sends him a look and turns back around. Reaching into his pocket, he switches it to medium and drops down to “tie” his boot.

“So, are you seeing anyone?” (Y/N) asks trying to be polite and keep her mind off of what’s happening in her pants.

“No, I would like to, but my schedule is crazy so I don’t really have time to go out and mingle. Are you?”

Dean was leaning on the basket, hitting her ass with it over and over again. She reaches her hand back, putting the back of it on her ass and holds the basket through the holes. It was subtle so, only they knew it was happening.

“Uh, yeah. I am. Actually, Jason, this is my…”

“Boyfriend. I’m Dean, how are you?” He straightened and stuck out his hand, standing beside her now.

Dean can feel (Y/N) grab the back of his flannel as she leans into him.

“Fine. I’m Jason. Her ex.”

Dean nods, pulling his hand back once the shake was returned.

Jason draws his attention to (Y/N), noticing how hard she’s staring at the floor.

“(Y/N), are you okay?” He moves a hand to her elbow.

“Yeah, yeah, I’m fine.” She replies a little out of breath. “I’ll be back. Dean watch my backpack please.” Taking it off, she places it in the basket.

Dean and Jason watch as she hurries off.

“Is she really okay?” Jason asks him.

“Yeah, she’s fine.” He says, knowing why she took off the way she did. His shirt can only do so much to level her.

“Hey, you’re the guy with that bakery.” Jason’s dark brows go down in thought.

“That I am.” Dean places his hand on the basket.

“How long have you two been together?”

Dean remembers Jason. He would come to (Y/N)’s place every now and then, passing by the shop when (Y/N) was about to come in to talk to Dean.

“We got together recently.”

After he says that he’s phone text sound goes off. Pulling it out of his pocket, he sees it’s from (Y/N).

_**My Bookstore Babe** _

**_Pls turn it off_ **

Dean does so and a few seconds after he sees her come around the corner. They make eye contact and (Y/N) smiles at him before looking at the floor.

“Sorry, I’m back. We should get going though. It was nice to see you again, Jason.”

“Yeah, I probably should too.”

(Y/N) hugs him, patting his arm. “Come by the shop sometime and get a book. Also, you should swing by Dean’s shop, he makes some killer pie.”

Jason nods, starting to walk backwards. “See you guys later.”

“See ya.” (Y/N) replies cheerfully.

Dean can almost laugh at the confused look on his face. When he’s out of view, (Y/N) draws Dean closer by his belt loops.

When their lips connect, she starts pulling and biting on his. They’re no doubt are going to be red. The longer they kiss, the more excited she seems to be getting and Dean has to pull back.

“I still need these, Baby.” He jokes, hands resting on her ass.

“I’m sorry. I just, ugh, oh my god. That was- I’m happy I bought these. More than happy. Ecstatic. When I texted you, I was in the next aisle just… I almost lost it when we were talking to him. Dean, that was amazing and I wish there was a way you could’ve felt what I did.” She puts her head on his chest, hugging him.

Dean returns the hug. “I think I’ll stick to how we usually do things. I think it would be noticeable if I was, um, feelin’ the same thing you were.”

(Y/N) sighs, happily. “I’m so glad we got together. Jason would’ve never agreed to this.”

“And that is why we are two different men. Let’s go so I can pay for this stuff.”

Once they finish up at the store, they find somewhere to eat. When they do, they find a booth in the back of the restaurant, where no one can see them. (Y/N) sits in one side of the booth and pulls Dean down beside her.

After they order, they sit and she tells him about closing her shop when he closes his, instead of being open two hours after. He asks why and she says not a lot of people comes in those two hours, so it wouldn’t hurt anything if she does. It makes sense.

The food arrives and they begin eating. Not able to help himself, Dean turns the remote on low. (Y/N) arches her back a little and continues eating. But when he switches it to medium, she stops eating and takes the closest arm to her. Dean swipes his thumb on her thigh. He begins going between high and medium.

Dean peeks out of the booth and sees no one is coming, swallowing what he has in his mouth, he has her lean against the wall inside the booth. Raising her shirt, he lowers one side of her bra, exposing one of her boobs. Her hand flies to the back of his head as he sucks and nips at her nipple.

“Keep it on high.”

Doing what he’s told, he feels her fingers tighten on the back of his head. After they loosen, he turns the remote off and draws back. He puts her boob back where he got it and pulls her shirt back down.

(Y/N) sits correctly in the seat, grabbing his chin, so she could kiss him. When they pull back, Dean winks and bites his burger, the waitress comes over and grabs their cups for refills.

“She woulda had one hell of a surprise if she would’ve came earlier.”

(Y/N) actually snorts and starts to laugh even harder from embarrassment. By the time she finishes, the waitress has already given their drinks back and left.

When all their food is gone, they head to Dean’s shop to put up his paintings. So he wouldn’t forget, he handed her the remote back when they were finished. She took it and put it in her backpack. Grabbing his hand, she pulls him to the back of the shop.

(Y/N) pushed him against the wall, before dropping to her knees. He watches as she unbuckles his belt and undoes his pants. Freeing his cock out of his underwear she pumps it a few times and licks the head, before taking it fully in.

As she bobs back and forth, Dean leans his head back, moving his feet a little further apart. He feels her hand grab his balls and tug them. Lowering his head, he sees her pulling off of his dick and lick at his shaft. (Y/N) looks him in the eyes before taking his balls into her mouth.

“Fuck, Baby…”

“Mmm, ya like that?” (Y/N) starts sucking at his tip, hand pumping his shaft.

“Love it.”

She moans and he can feel the vibration. Pulling back, (Y/N) continues to pump his cock and watches as precum comes out.

“I wish this was inside me right now. Could you imagine me in your apron bent over that table over there? Pounding in me from behind? Making me speechless as you choke me? Or, beg you not to stop like I did the first time you fucked me? I couldn’t believe how big your cock felt. Before I met you, I wasn’t one to suck dick, but yours… It’s just something about it. Look at that.” She’s referring to how red his tip is and how his cock jumps at her thumb going against it.

Dean can feel pressure building up inside him.

(Y/N) closes her mouth around him again, but when she gets to where she usually stops, she keeps going. Feeling himself in her throat has him cumming with his head thrown back. She pulled back to the tip and tugged at his balls, milking him of all he’s got.

Dean grabs the hand she still had on his cock and pulled her up.

Most guys don’t kiss someone after they’ve sucked them off, but Dean’s thing is, if you’re not kissing them, then you might have something you need get check out if you don’t want to taste yourself. But that’s just him.

Dean was tucking himself back in as he lapped at the taste of himself. She pulled back smiling.

“I’ll take that as I did good.”

“Good? That was fantastic.” He finishes fixing his clothes.

“I thought I should reward you for today.” (Y/N) goes to her backpack and puts it on.

“That it did… That it did.”

They’re in the car and Dean can’t help but to ask.

“Is it true?”

“Is what true?”

“About you not, uh,” The does the gesture for sucking dick.

“Oh, yeah. If any guy I was with before asked me to do it, that would’ve been a no go. That weren’t hittin’ it that good.”

Dean nods, looking out the front window. He doesn’t show on the outside how proud of himself he is, but talk about an ego boost.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!!


	4. Chapter 4

Dean was talking to a customer at his display counter and (Y/N) walked in. He was listening to what the woman saying about not being able to probably make her dough, while (Y/N) stood to the side with a smile and a see-through shirt.

“I’m sorry, could I speak to her for second and I can come back and tell you what you’re doin’ wrong with your dough?”

“Oh, yeah, that’s fine.” The woman leans on the top of the display.

When they get back there, Dean takes her by the ovens.

“What is this?” He asks, flicking the bottom of her shirt.

“My shirt…?”

“Why can I see through it?”

She huffs, looking down at herself. “Because that’s how the shirt was made…”

“I get that, but I don’t get why you don’t have a tank or somethin’ under it.”

(Y/N) grabs her arm, looking off to the side.

“It’s not just me who sees you every day or just sees you in general. You’ve basically put on your bra and said, “fuck it”.” Dean moves her head so she’ll look at him. “I’m not knockin’ how you look in it. I think you look good. But I just want you to understand shirts like this can make a man think. You’re not leavin’ anything for the imagination like this. The only people who should know how all this looks at this moment is me and you. Don’t you agree?”

“Yes.” She says quietly.

“So, grab my jacket and put it on before we go back out.”

“But Dean-“

“Put. On. The. Jacket.”

“Yes, Sir.” She says sarcastically, rolling her eyes.

Dean watches with his arms crossed as she walks over and shoves her arms through. (Y/N) tries to walk past him, but he grabs her arm. He zips up the jacket, looking directly into her death glare.

“Get what you want out the thing and I’ll make your drink.”

They get back out and Dean begins talking to the woman he was before, while he makes (Y/N)’s drink. He hands it off to her and watches her walk towards the door. She shoves open the door and since the door closes kind of heavily, it kind of slammed shut. When it slammed, the sign he has on the door came off and she just looked back and quirked her brow.

The customer looks back at the door and looks at Dean with her brows raised.

“Girlfriend?”

“Yeah.”

“Ah.”

 

Lunchtime comes around and he flips the sign he had to pick up. Going next door, he opens the door and sees (Y/N) come into view with the jacket off.

“Get your ass back there.” He says through his teeth, loud enough for her to hear, as he flips her sign on the door.

Dean turns the lock on her door and makes his way to the back.

She was leaning her ass on a table, staring at the ground, but looked up when he walked in.

“I guess I’m in trouble?”

“What do you think?” He questions, staring at her.

(Y/N) wanted to see what it would be like if there was sub/dom in their relationship. There hasn’t really been any situations for them to use it to really get a feel for it. Except now.

“Pants down.”

Her head kind of cocks to the side like she didn’t hear him right.

“Do I need to do it for you?”

(Y/N) quickly straightens up and undoes her jeans, sliding them down her legs.

“Panties too.” Dean continues to watch her with his arms crossed. She hooks her thumbs under the waistband of the panties and slowly pulls them down.

“Turn around and bend over the table.” She does so slowly.

Dean comes closer to her, standing beside her.

“So, you wanted to have an attitude earlier?”

“No, Sir.” She states quietly.

Dean slaps his hand against her ass, it catches her off guard.

“You had an attitude earlier, correct?”

“Yes, Sir.”

“Why is that?”

“I didn’t want to put on the jacket.”

When Dean takes a look at the side of her face, he sees she’s smiling at her hands.

“Since you think this is funny, I got something else for you.”

At the sound of his belt buckle coming undone, (Y/N) looks back with wide eyes. Dean joins the ends of the belt together.

“Turn your head back around.” He tells her calmly.

(Y/N) does as she’s told, putting her head on her arms and slightly sticks her ass out a little more.

“You made the sign come off my door.” The belt makes contact with the back of her thighs. “And you kept goin’.” Another hit. “You were mad ‘cause you didn’t want to cover up.” Another hit to her ass. “You were showin’ everybody what’s mine.” The fifth hit makes contact. “What were you thinkin’?”

“That you’d see me in it.”

Dean puts his belt beside a stack of books on the table. “You knew I’d react this way?” He lays a hand on her ass.

“I got a better reaction than I thought I would.”

Raising his hand, he smacks it back down. “So, this is what you wanted?”

“Yes, Sir.”

Dean’s hand sinks further down between her thighs. He sinks his middle finger into her pussy, feeling how wet she is.

“You’re this wet from just from me spankin’ you?” Dean sticks another finger in, hooking them a bit. “What’s the real reason you did this?”

She moves back on his fingers. “I wanted to see how possessive you’d get.”

Dean can’t help, but to smirk. “How’d you know I was possessive?”

“Most dominate types are.”

He removes his fingers and turns her around to face him. Placing his hand back where it was, he puts his other on the table to sort of trap her.

“I come off as a dom to you?”

“Yeah…”

“Hm.” Dean watches his fingers rub at her clit. “How?”

(Y/N) looks down to where Dean’s hand is, not responding. So, Dean stops and waits for her to talk.

“B-because you know how to take control and you take care of me.”

“That’s it?” Dean asks, speeding up his hand.

“I-it’s hard to explain…” She squeezes her eyes shut and he sees her hands grip the table tighter.

“Or you just like someone who knows what they’re doin’. You like it when I manhandle you.” Dean gets closer to her ear. “When I fuck you so good you can’t even think straight. Like now, I’m just usin’ my fingers and you can’t even keep your eyes open. But do you know what I like the most?” He asks pulling back.

She shakes her head as she bites her lip.

“How your body tightens up just before you lose it. I can feel it on my fingers right now. And you wanna know the craziest part about right now?”

“Yeah…” (Y/N) moans.

Dean removes his fingers and steps back, after picking up his belt. “That I’m not gonna let you finish. Since you purposely wore that shirt to get a reaction, I’m gonna purposely not gonna let you finish.”

Her eyes snap open and she looks at him in disbelief.

“Pull up your clothes, lunchtime is over.” Dean turns and heads to the bathroom to wash his hands.

When Dean comes back out, he goes to the front part of the store to see (Y/N) sulking in her chair with her arms crossed, staring out the shop door, jacket on. He leans on the counter in front of her, smiling.

“See what happens when you wanna have an attitude? Now you have one for real.”

She doesn’t say anything as she stares at him.

He laughs. “You’re gonna make me go back over without my kiss?”

The side of her lip twitches up.

Dean reaches over and pulls her forward. “Come on, you know you wanna.”

(Y/N) pecks his lips.

“That’s all you’re gonna give me?” He whispers, eyes half closed.

After a few more pecks, (Y/N) allows him to slip his tongue into her mouth. Dean controls the kiss and (Y/N) has a hand on the back of his neck.

Dean sucks her bottom lip as he’s pulling back.

“I’ll make it up to you later.” He whispers.

Making his way towards her door, he unlocks it.

“Oh, and when I come over to your place, I don’t expect you to have any clothes on.”

(Y/N) nods, trying to contain the smile Dean knows wants to come out full force.

“Yes, Sir.” She says, once he raises his brow.

Satisfied, Dean makes his way back to his bakery.

This sub/dom thing should work out nicely.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!!! <3


	5. Chapter 5

Dean arrives at (Y/N)’s apartment. He walks slowly to her door, nodding his head to a gentleman passing him. 

Fist raised, he knocks on the door and steps back. 

He hears the chain slide off and the lock turns before it opens. Her head pokes around as she opens the door further to let him in without letting herself be seen. 

Dean comes into the apartment and while she closes and locks the door he puts his keys, wallet, and phone on the coffee table. 

(Y/N) did what he said. She has absolutely no clothes on. 

“Where’s your lotion?” Dean asks rolling up his sleeves. 

She looks at him strangely. “Why do y-“

“Where?” 

“In my room…” (Y/N) states, shifting, feeling awkward standing naked in the middle of her living room. 

“Lead the way.” 

She begins walking with her arms crossed in front of herself. Dean trails behind her, smirking. 

“Right there.” She tells him, pointing to some on top of her dresser. 

Dean looks through them, smells a few, and finally picks one that doesn’t have a perfume scent attached to it. 

“Lay down on your stomach.” He says, shaking the bottle. 

When she lays on the bed she tucks her arms under the pillow her head is on. Dean sits on the bed and squirts some of the lotion on her back, chuckling a bit when she gasps at the coolness of it. 

He begins to slowly rub the lotion in, adding pressure here and there. She seems to sink into the bed with her eyes closed. Dean rubs his thumbs in circles into her lower back. Hands sinking lower, he begins to massage her glutes. 

In her mind, she probably thought he was going to walk through the door, pick her up, and carry her to the room to finish business. But, no. That’s not what he has in mind. Who doesn’t like a nice almost full body massage? 

“Flip for me.” 

He takes his hands back to himself. She flips slowly, smiling at him. 

“I didn’t know you gave massages.” She closes her eyes again, exhaling. 

“Well, I may be a baker but there’s more than two ways I use my hands.” Dean comments, starting on her torso. 

(Y/N) huffs a laugh. 

He doesn’t pay as much attention to her front like he did her back. 

“I’m gonna head to the bathroom.” 

“Okay… Should I put something on?” 

“Did I tell you to put somethin’ on?” Dean retorts, quirking his brow at her. 

“No, Sir.” She responds. 

Dean comes back over to the bed and begins to kiss her. 

“Just relax, I’ll be back.” He whispers as he pulls back. 

She nods, swallowing. 

Dean closes the door of the bathroom. He doesn’t need to relieve himself, he’s actually looking for something. Fiddling with a basket she has sitting by the sink he finds what he needs and puts the item in his pocket. Dean flushes the toilet and turns on the water, so she’ll think he used the restroom. 

When he comes back, she’s still laying there. 

He returns his hands to her body. 

Taking one of her hands, he begins to massage it. 

“I never realized how soft your hands were.” He says quietly. 

That’s the only thing that breaks the silence in the room. He sets her hand down on her stomach and grabs her other one. Reaching into his pocket, he pulls out what he stuck in there earlier. He places the hand down beside the other. 

Dean binds her wrists together. 

“What?” (Y/N) states shocked. “This was in my-“

“I know where it was.” Dean states calmly. 

What Dean took in the bathroom earlier was a headband. It was one of those thin black ones that has a good stretch to them, but when you twist it to make it look like a ponytail holder that stretch is long gone. He knew she had it because he sees her wear it here and there. 

“Now, what you’re gonna do is listen. That means no talkin’. Understand?” Dean questions, staring her down. 

“Yes, Sir.” 

“Apparently, you don’t because I just told you not to talk. We’re gonna try that again. All you’re supposed to do is listen, mouth closed. Understand?” He tells her with a bit more bark in his voice. 

She nods, biting her lip. 

“Earlier I told you that I was gonna make up for not lettin’ you finish. That massage I just gave you was it.” 

(Y/N) looks off towards her dresser. 

“I’m not over there, I’m over here.” 

Her eyes snap back to his. Dean makes no comment on how her hands are opening and closing and her chest falls follow their pattern. 

“You really thought I was gonna let you off easy. Not only, what you did was childish, it was also disrespectful. There were customers in my store and you wanted to act a fool.” 

“Sorry.” She instantly realizes her mistake. 

“You know that sayin’ “three strikes you’re out”? Well, you got one more.” Dean says from his spot by her thighs. 

(Y/N) gives him a jerky nod. 

“Since lunch, I’ve been thinkin’ of ways to punish you. I thought about no sex for a week, but that punishes both of us. Not lettin’ you cum for a week, but you could easily do it without me. Then I said to myself, “the punishment is obvious”.” 

Dean stands, taking off his shoes. He unbuckles his belt and drops his pants and underwear. Taking both of his shirts and socks off, he sits back where he was. 

“You’re not gettin’ my cock, but you can see it. See how hard it is, but not feel it. Watch me, thumb at my slit. You know what? You’ll get it eventually, but you have to tell me why you should get it. But that’s not right now. For now, you’re just gonna watch me.” 

Dean gets up, stroking his cock. He grabs her bind wrists and moves them above her head. 

“I want you to be able to see everything.” 

Dean picks up the lotion and puts some into his palm. He slowly jerks himself as he moves closer to her. Just to mess with her more, Dean starts to tease her nipples. 

She closes her eyes. 

“I thought I said watch me.” Dean comments, squeezing one of her breasts. 

(Y/N) gasps, snapping them back open. Her pupils have become bigger than usual. 

Dean’s eyes trail down her body, until he lands on her legs. She has her legs closed tight, so her clit can get some type of pressure. Placing his hand between her thighs, he separates them. Dean licks his lips before sticking his index and middle finger into her pussy. 

“Can you hear how wet you are?” He was moving his fingers back and forth. 

Nodding, she almost shifts, but stops herself. 

Dean retracts his fingers. 

He hears a whine. His eyes connect with hers and one of her thumbs are rubbing the opposite hand. 

“You ready to tell me?” 

She nods quickly. 

“Why should I let you have my cock if this is a punishment?” 

“Because I know better now.” 

“Know better about what?” 

She moves her arms a bit. “That I shouldn’t try to pull reactions out of you and that I shouldn’t pull that kind of shit in front of your customers. It makes you look unprofessional.” 

“That’s the only thing you got out of it?” 

“Yes, Sir.” (Y/N) responds, shyly. 

Dean nods, moving to kneel in between her legs. She spreads her legs further apart for him to fit. He guides himself in. 

Going forward, he hovers over her, bringing her arms down to hang around his neck. 

“Listen, I’m not attracted to you for this. I’m attracted to you for the person you are. And if you want me to be rough with you all you gotta do is ask.” He makes a sharp thrust, making her breath catch. 

“But one thing you will not do, is show your body off the way you did.” Dean starts to thrust in and out slowly. He dips his head down into her neck, biting and nipping. “You wanna show somethin’ off? Show ‘em this.” 

A moan falls from her mouth as he starts to suck on her neck. Her legs wrap around him. 

When he pulls back he places a kiss on the hickey. 

Dean pulls himself of out of her arms and carefully out of her pussy. 

“Oh, Baby, I’m not done.” He tells her when she whines for the second time this night. 

Getting off the bed, Dean has her move her own position. Her feet hang off the side of the bed and she’s on her elbows and knees. He’s standing up on the side of the bed. Reinserting himself, Dean takes hold of her hips. 

Pounding in, her shouts motivate him. 

He feels her walls constrict around him. 

“You already ‘bout to cum?” He questions breathing heavily. 

The only reply he gets is a broken moan. Thirty seconds later she cums, only held up by the hands on her hips. Dean keeps going though. He keeps going until he has to pull out. Flipping her on her back, he releases himself on her stomach. 

Both are still catching their breath when he shoves his fingers into her pussy. Finding her g-spot, he takes his other hand and rubs on her clit as fast as he can. 

“Dean… Oh… I’m gonna… Wait.” She tries to grab his arm, but can’t keep her hands open long enough. 

Dean watches as her eyes roll back and she throws her head further into the pillow, along with her back arching. She squirts onto his hand and on the sheets. 

Her breaths sound a bit like she’s laughing. 

Dean frees her wrists, proud of the work he’s just done. 

When she’s able to find words again, she looks at him with a bliss covered face. 

“I’ve never done that before.” 

Dean is confused about what she’s talking about for a split second. 

“You’ve never squirted before?” 

She shakes her head with a smile and a breathless laugh. (Y/N) rubs at her wrists over the imprints. 

“It’s messy but it’s worth it.” Dean says looking at the wet sheet on the bed. 

(Y/N) looks to but she’s so indifferent about it. 

“Come on. Let’s get cleaned up.” Dean takes her hand and drags her into the bathroom. 

After they’ve cleaned up everything, Dean stays and cuddles with her until it gets really late. 

Things almost start up again as he’s heading for the door. Five lip bites later, finds him sitting alone in his car, not really wanting to go home. 

**Notes for the Chapter:**

> Comments ad kudos are always welcomed!!! <3


	6. Chapter 6

Dean was at his parents’ house for their weekly family dinner. His mom’s parents where there: Deanna and Samuel. His father’s dad: Henry. And lastly, his younger brother Sam was there.

They were all sitting at the table eating.

“How’s your bakery?” His grandmother asks.

Dean swallows some spaghetti he just ate. “It’s great. Business is gettin’ better and better every day. I might have to hire someone so I can get a break every now and then.”

“I’m glad to hear that.”

“How are things going with (Y/N)?” Sam asks.

Dean looks at his brother and his hidden smile. Sam knows Dean hasn’t told their parents about her. It’s just because he doesn’t want them to meet her and make things awkward. He doesn’t want to say the wrong things or make the wrong moves.

“Who’s (Y/N)?” John asks his son.

“Uh, (Y/N) is a woman I’ve been seein’.”

“For how long now?” Mary is very much interested.

“Month and a half.”

“A month and a half and you haven’t brought her over?” She says in her motherly tone.

“It’s soon. I’ll bring her eventually just not now.”

“Let the boy live his life and when he’s ready you’ll meet her.” Henry says in his elder grandson’s defense.

“Thank you.”

“I bought your grandmother to my folks when we started dating.” Samuel tells him.

Dean’s ninety-nine percent sure that his grandfather didn’t get his relationship started by fucking in a bookstore, but he doesn’t actually want to think about that.

“Well, that was you. It’s kind of a different generation now. Things won’t be the same.”

“Yeah now, you boys don’t know how to act when y’all see a beautiful young lady. Where’d y’all meet?”

Dean clears his throat, done with eating. “She’s, uh, she’s the owner of the bookstore that’s next to me.”

Mary gasps. “I’ve been in there, she’s so sweet. I’ll have to go by there again.”

“Please don’t.” Dean whispers to himself. Sam hears him and chuckles.

His phone vibrates in his pocket and he pulls it out.

It’s a photo text from (Y/N).

He opens it and keeps his facial expression neutral.

She has sent him a picture with a collar on and connected to the collar are two nipple clamps on chains. The rest of her body is bare.

Right after he examines the photo his phone rings.

“I gotta take this.” Dean gets up and walks away from the table into the den.

When he puts the phone to his ear, he hears her breathing a bit heavily.

“What a thing to answer the phone to.” Dean comments, going into the backyard.

 **“Hey, what are you doing?”** She asks.

“I’m at my folks house.”

**“Oh, I’m sorry. I’ll call you later.”**

Dean looks over his shoulder. “No, it’s okay. I’m not doin’ nothin’.”

**“Okay…”**

The picture he received pops up in his head. “You playin’ with yourself while you talk to me?”

**“Yes, Sir.”**

“You havin’ fun without me?”

**“I needed to hear your voice. I went and got this collar today and all I could think about was you.”**

Dean licks his lips, walking further into the backyard. “Is the collar the only thing you bought?”

**“No, Sir. I bought a dildo. I-I had to get it an inch smaller than yours because they were out of your size.”**

He smirks. “Is it doin’ the job?”

**“No, Sir. That’s why I called you…”**

“You’re thinkin’ about me comin’ over, shovin’ my cock in you?”

**“Yes, Sir.”**

“I come over then what? I fuck you into the mattress? I take it slow? Or do I let you ride me? Should I choke you and bend you over?”

(Y/N) doesn’t actually respond as her breathing increases.

“You like that last one, don’t you?”

**“Mhm.”**

“Figured. I come over this is what will happen. I’m gonna fuck you against the wall. I’m not gonna stop until you can’t walk straight. I’ll probably leave a bruise or two haven’t decided yet. You want me to cum in you or on you?”

 **“In me…”** She says quickly.

“Oh, you wanna feel my cum drip out of you. Round two… on second thought, you probably wouldn’t make it for round two.”

**“W-what would happen on round two?”**

“You really wanna know?”

**“Yes, Sir.”**

“Since the first round was rough I’ll give you a break. I’ll stick my tongue in your pussy and suck at your clit. You want me to, I’ll stick my dick back in you. Long deep strokes while I hold you in my arms. For round two we wouldn’t be fuckin’. We’d be makin’ love. I’ll take in every piece of you, worship your body, and we’d come together.”

On the other end of the phone throughout him speaking, (Y/N) was moaning then it cut off, but he could still here something wet on the other end. Her breathing turned into sounding like she was trying to catch her breath. Dean heard her sigh as he looked at the back doors of the house.

 **“Would you stay after we made love?”** She asks almost sounding fragile.

“I wouldn’t even think about goin’ anywhere else.” He responds honestly.

It’s quiet between them for a minute before Dean asks, “How long are you stayin’ up?”

 **“I don’t know. Why?”** She asks quietly.

“’Cause Daddy’s comin’.”

The last thing he hears before he hangs up is her gasp.

**Notes for the Chapter:**

> I wrote this whole chapter just so I could fuckin' use Dean's last sentence. It was time greatly spent. That's why the chapter is short.
> 
> Comments and kudos are always welcomed!!! <3


	7. Chapter 7

Dean’s leaning on the doorframe when she answers the door. He closes it behind himself when he walks in, puts the chain on the door, and looks at her as he flips the lock.

She’s slowly backing up in her bra and thong, looking up at him.

He undoes his belt and pants. Instead of pulling his clothes off, Dean takes out his dick, giving it a few strokes. Backing her up into a wall, Dean smacks a hand on her ass, giving it a firm squeeze.

“You really thought I was just gonna let you call me and not come over. You bought that dildo when you could’ve had the real thing in the snap of a finger.” Dean licks his lips, taking a small step back. “Take the thong off.”

(Y/N) inches them down, kicking them to the side.

Catching her by surprise, Dean picks her up and maneuvers his forearms under her knees. Spreading her legs wider apart Dean puts the tip of his dick in front of her pussy. She reaches down, helping him insert it.

Dean traps her against the wall with a better grip on her. Pulling out he slams back in, starting his punishing pace.

(Y/N) has a hand full of his flannel and her other hand is on the back of his neck.

“You remember what I said to you before I hung up?” Dean pants, looking at his dick disappear.

“’Daddy’s comin’”.” She switches the hand that was on his neck to the back of his head.

“Yeah and you couldn’t wait for Daddy to come, huh?” He whispers, lips touching hers.

“No, Sir. I couldn’t want for you to come and fuck me.”

Dean smirks, capturing her lips in a kiss completely opposite of the pounding below. Changing his hold, he brings her closer, changing to sharp thrusts instead.

He feels her body beginning to tighten.

“You came earlier to the thought of me doin’ this. Don’t bit your lip, I wanna hear you. You still want me to cum in you?”

She nods, moans and whines coming from her.

“You gonna make it to round two?”

“I-I can make it to round two.” Her eyes close.

“You sure?”

“Yes…”

“Yes, what?” Dean feels himself getting close.

“Yes, Daddy…” Right after she says that, she come with a shout.

Dean’s still fucking her as she shakes from her climax. The last thrust in he holds her there, capturing her lips again.

Pulling his dick out, he sets her feet on the ground.

She leans on the wall and seems to almost start sinking down.

“Woah, I got ya.”

Dean picks her up bridal style and carries her to the bedroom. He sets her on the bed. When he straightens up to take off the rest of his clothes, Dean notices her hands are shaking.

“Baby, you okay?”

(Y/N) sits up, bringing her shaky hands behind herself to take off her bra. “Yeah, I just- aftereffects, ya know?”

Dean nods, beginning to take off his clothes. “You know we don’t have to do round two, right? We could do it some other time.”

“I wanna do round two, but I wanna clean up first.” She scoots to the edge of the bed, legs visibly shaking.

“You got it by yourself?”

“Yes, Sir.” She makes her way towards the bathroom.

Dean wipes his dick off with his flannel, tossing it to the side. He waits for her sitting on the side of the bed. When she comes back, her shakes are gone and she’s smiling at him.

She climbs in his lap, initiating the start of a make out session.

Dean flips them, so that she’s spread out under him. Moving from her lips, he kisses under her chin. Dean makes slow progress mapping out her body with his lips.

“If I knew you liked to be called, ‘Daddy’, I would’ve been said it.” (Y/N) states with a hand on the back of his moving head.

“Then I guess you know to call me Daddy from now on then. Sir, is just as good. Whichever you feel like sayin’ is fine, Baby.” Dean says, leaving kisses just under her belly button. He finishes with his kisses and proceeds to use his hands to do the rest of his mapping.

Kneeling off the bed, Dean puts her legs on his shoulders, pulling her closer to himself.

He keeps his promise, sucking his tongue inside her. As he slowly flicks his tongue, he holds her hips down.

“When we first met, I wanted you to fuck me so bad, but I was with Jason. Mmm, I wouldn’t have ever imagined we would be in this position.”

Dean doesn’t respond, he just moves his mouth over her clit. (Y/N) grinds as best as she can with a hand full of Dean’s hair.

He feels himself grow hard once again the more she moans. Taking one of his hands off of her, Dean reaches down and begins stroking himself.

“I could do this all day.” Dean whispers, pulling back to swallow, tongue going back in.

“Can I have your cock now, Daddy?”

Dean’s ears kind of perk up like a dog. He pulls back, telling her to lay her head on the pillow. Above her, he gently puts his dick inside of her. Dean maneuvers an arm under her, holding her as close as possible.

With her legs around him, he pulls out as far as he can, before slowly thrusting back in.

(Y/N) keeps their foreheads connected with a hand on the back of his head.

This is actually the first time they have been “intimate”.

He sort of thought that they wouldn’t get to experience it because he thought (Y/N) would only be interested in the manhandling and pounding way they usually do things. But with the way she asked if he would stay after, has him thinking maybe she thought the same about Dean. Maybe she wants to know if Dean is one thousand percent in the relationship. Even though he told her he wasn’t in it for the sex, actions are still louder than words. It’s hard not to think if either one of them are in it for the sex or not because that’s how their relationship started in the first place.

“Dean, I’m close.” She pants in the space between them.

“Hold on for me, Baby.”

She slightly nods, biting her lip.

(Y/N) does exactly that as Dean feels himself getting closer and closer, he seals their lips together, arm tightening around her.

As they both cum, Dean places his face into her neck. Before he pulls out, (Y/N) places her hands on both sides of his face, giving him the most passionate kiss they have ever shared.

Later after they have cleaned up, Dean holds her in his arms as they both drift off to sleep.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	8. Chapter 8

Dean picked (Y/N) up for their date tonight. They were going to the movies.

She looked nice, dressed in a black blouse that cut low and she had on a burgundy mini skirt.

Dean was dressed in a sky blue button down that he rolled the sleeves up on and he had on some dark jeans that didn't have worn out holes in it.

They never discussed what they were going to see, but he knows they'll come to an easy agreement once they get there.

Arriving at the theater, Dean gets out and opens her door.

Walking hand and hand up the stairs, they stare at the huge wall of movies being showed.

"What do you wanna see?" Dean asks her.

"I don't know. What do you want to see?" (Y/N) leans into him some more.

Dean continues to stare at the wall before him. He smirks and drags her over to the window.

"What are we seeing?" She questions excited.

"You'll see."

The line finally moves down enough for their turn to arrive.

"Hey." The cashier says to them.

"Hey, could I get two tickets to Fifty Shades Darker?"

"That will be $20.58."

Dean hands over his card and glances at (Y/N). She's staring at the girl rip out the tickets.

"Here you go, Sir. Enjoy."

"Thank you."

Making their way into the lobby of the theater, Dean hands the tickets to the man standing there. He rips whatever he has to rip off of them and hands them back with a smile.

They stand in line at the concession stand. Dean takes back his arm she was latched onto and gently navigates her in front of himself.

“Do you wanna share some popcorn?” Dean asks, dipping low next to her ear.

“Yes.”

Another friendly face greets them when there turn comes.

“Hey, could I get a large fruit punch and a large popcorn?”

“Yes, Sir. Is that it?”

“Get what you want, Babe.”

“I’ll take a fruit punch also and a box of Reese’s Pieces.”

Dean pays for the items and he asks her to get some napkins. While she’s gone, he takes the lid of his drink and dumps out some of it into the water fountain he stopped by. He puts the lid back on as she turns around.

“Uh, I get kinda messy with popcorn, can you get some more?”

“Sure.”

When she walks back off he takes it off again and dumps the rest. She takes his arm and they make their way to the movie. They take seats at the very top.

The movie starts and he relaxes.

Dean’s not paying attention. Ask him a question, he wouldn’t be able to tell you what the hell is happening. He didn’t even see the first one. There was no reason for him to. The only reason he’s seeing this one is because he’s seen the book off to the side in (Y/N)’s bedroom. He doesn’t know which book it was, he just knows it was a Fifty Shades one.

(Y/N)’s eating the popcorn, watching the screen like the few other people in the theater. The movie’s been out for a while now, so almost everyone has seen it already.

Leaning over, Dean places a kiss on her cheek. (Y/N) looks at him, swallowing the popcorn she had in her mouth. He looks her up and down, biting his bottom lip. She kisses him, hand going to the back of his head. As their kisses get heated, Dean takes the popcorn bucket out of her lap and sets it on the floor.

“You got somethin’ on under this?” He lifts the mini skirt just a tad to indicate what he was talking about.

“Yes, Sir.”

“Take it off.”

Grabbing the bottom of her mini skirt, she pulls it up, rocking side to side, sliding down the thong she was wearing.

Holding out his hand, she gives it to him and he shoves it in one of his front pockets.

“Keep your hands on the armrests.”

“Yes, Sir.”

Dean takes her drink and puts it in the drink holder in the seat beside him. He taps two fingers on her lips, telling her to open her mouth. Mouth opened his slips them inside and he feels her tongue swirl around them.

Pulling them out, he drops them between her legs, teasing her clit.

“Can I see your cock?” She asks in a soft alluring voice.

He licks his lips and looks down at his crotch, before eyeing her with a smirk. “You wanna see my dick, get it out yourself.”

(Y/N) lifts his shirt from over his belt. She’s trying to stay quiet as she unbuckles it. With his pants undone, she reaches into his underwear and pulls out his hard member.

“You want me to fuck you in here?”

Her eyebrows shoot up. “In here?” The question has a slight excited twist at the end.

“Yeah, I’ll take you right now.” Dean leans over, placing kisses on her neck. “You’ll have to be quiet, can’t let ‘em hear us.”

“I can do that.” She tells him still holding his cock.

He pulls back, lips on hers. “You can do that?”

“Yes, Sir.” She whispers.

Dean straightens in his seat. “Get up and show me.”

(Y/N) bites her lip, looking at the other patrons. Finally, she gets up and Dean spreads his legs for her a little more. Between his legs, he helps her guide herself on his dick.

“Hold on, Baby.” Dean reaches for the many napkins he had her get. He places them down to catch anything that may stray. “’Kay, let me have it.”

She leans over the seat in front of them.

The movie is just background noise at this point. Dean gives her praises as she moves up and down on him.

After a few minutes of her quiet movement, Dean has enough of not doing anything.

When she’s all the way down he wraps his arm around her waist and brings her back against him. He makes her grind on him as he pulls her shirt up to expose her bra; he pulls both of her breasts out.

Not knowing how much of the movie was left, Dean speeds things up.

Scooting down in the seat, he takes the same two fingers he had her suck earlier back down to her clit. A moan slips out of her mouth and Dean quickly clamps his hand over it.

“You almost made it. We’re gonna hafta practice.”

(Y/N) nods jerkily, hands gripping the armrests.

“You gonna cum for me? Cum on my dick? I wanna fill you up so bad right now, you got no idea. Your little outfit put all kinds of ideas into my head.”

Adding more pressure on her clit, (Y/N)’s hands snap down on top of his and she draws up her legs. Dean tightens his hand on her mouth as she whimpers.

“Shhh, Daddy’s got ya.” Dean whispers as her back arches. Her legs begin to go down and her body loosens. “That’s my girl.”

He takes his hand off her mouth and she slowly pulls off his dick. Dropping in front of him, (Y/N) grabs his shaft and places her mouth around his tip.

Dean removes the napkins he placed down, balling them up in one hand.

“Can’t get it one way, you’ll get it another.” Dean says, caressing her cheek.

She hums in agreement. Not long after Dean cums, biting his lip and she makes sure he’s finished before pulling off.

(Y/N) returns to her seat and Dean pulls her into a kiss. They clean up with the napkins they have. She’s holding her napkins, not knowing where to put them. Dean grabs his cup and takes the lid off, tossing his in. (Y/N) puts hers in with a smile on. He puts the lid back on and puts it in the holder. Returning her drink from where he got it, he bends down and grabs the popcorn, putting it in his lap.

She takes the arm closest to her and curls up as best she can in the seat, laying her head on his shoulder. Dean rubs his hand back and forth where she placed it on her thigh.

They sit through the rest of the movie in that position. When the credits roll around, Dean pats her thigh. She doesn’t move, so he looks at her face and sees that her eyes are closed.

“Baby, it’s time to go.” He says before laying a kiss on her head.

Her head rises and she stretches. They get up and Dean makes sure she grabs her unopened box of candy.

He dumps their unneeded items into the trash and wraps his arm around her waist, making their way out of the cinema.

Dean opens her car for her, then makes his way to the driver’s side of the car. Inserting the key, he looks at her and says, “So, what was your favorite part?”

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!!<3


	9. Chapter 9

Right now, Dean and (Y/N) have a bit of a game going. Dean likes to call it, “How long will she last?”. The game rules are:

  1. No Sex; of any kind
  2. No kisses longer than a peck; only on the lips
  3. No masturbation



Other than that, it’s free game. You do whatever you have to to get the other person to break first. There’s no loser gets this and the winner gets that. They’re just playing to see who can hold out longer. And so far, Dean is winning.

He’s lacing up his boots when his phone goes off beside him. Picking up the device, he huffs when he sees (Y/N) sent him a picture of her tits.

Dean begins writing:

_**I bet you can’t wait for me to suck on ‘em.** _

And he sends it off.

Having everything he needs, Dean heads to his shop to start baking for the day. When he gets there, (Y/N) is sitting in her car.

“Hey.” He greets with a bright charming smile.

She stares at him, before shaking her head, closing her car door.

“How?”

“How what?”

“How do always manage to flip it?”

“You could call it a gift. I don’t know.”

“Gift my ass.” She mutters, walking ahead of him.

“Well, your ass; I consider it the perfect gift.” He finds his shop key.

“Shut up. You will not win.” Dean watches her walk into the shop before him.

“How many times have you convinced yourself of that?”

(Y/N) opens her mouth just to close it again.

“That much?” Dean chuckles, taking off his jacket and over shirt.

“You’re acting real cocky right now.”

“It’s not that I’m bein’ cocky. It’s just that I know what makes you wet. Like how sometimes I’ll call you: Baby or Babe. Or I’ll give you a certain look or say somethin’ in a certain way…” Pausing his actions, he strolls over to her. “Like now, I know you wanna kiss me, but you can’t because then you’d lose. ‘Cause just a peck isn’t enough. You want me to put my hand down your pants and play with your pussy. Or drops to my knees and eat you out, right? Better yet, I could pick you up and fuck on the counter.” Fully closing her against the wall, Dean says, “As much as I’d love to do all of those things, I can’t. Because I refuse to lose…” He whispers the last part a hair away from her lips before backing up with a smile, throwing on his apron.

“Let me get this stuff together and I’ll fix your coffee.”

“That’s fine. I’m just gonna go straighten up my books and stuff.”

Dean contains his smirk. “You want me to bring it over when I’m done with it.”

“Um, yeah, that’ll be great.” (Y/N) hurries out of the kitchen.

Whistling, he gets to work.

 

Things in the ovens, Dean takes off his apron and fixes up (Y/N)’s coffee. When he gets into her shop she’s standing up reading.

“Here.” Dean places it on the counter.

“Thank you.” She continues to read.

“Can I get the kiss I haven’t gotten today?”

“Hm, I don’t know. I just might lose.”

“I mean if you think so…”

(Y/N) grabs his shirt and pulls him in for a kiss.

“Get out of here.” (Y/N) says not hiding her smile well.

“As you wish.”

Almost making it to the shop door, (Y/N) stops him.

“That’s cheating.”

“What’s cheatin’?”

“Grabbing my ass.”

Dean smirks, chuckling a little. “Baby, there are three rules and a ass grab isn’t one.” Winking, he walks fully out.

 

Sitting behind his display case with a worker he hired, Dean was scrolling through his photos. He has to quickly turn his phone slightly to the right, so Pat couldn’t see what’s on his phone. Absently glancing at his patrons, Dean decides to send the photo off to (Y/N).

A costumer just sat down, when she comes in with the biggest grin.

She comes straight towards him on the other side of the display.

“I win.” (Y/N) states, folding her arms on top of the glass.

Shoving the phone in his pocket, Dean gets up, doing the same. “How?”

“Because you said no-“ She looks at Pat before putting her hand up by her mouth. ‘Masturbating.’ She mouths.

“Who says that’s recent?”

The question makes her pause with a furrowed brow. “That’s not fair…” (Y/N) whispers.

“It is fair.” He gets closer to her face. “You called me a cheater, I’ll show you one. Follow me.”

Dean takes off his apron, telling Pat he’d be back. (Y/N) trails behind him like a lost puppy, right back out of his shop and into hers. Pulling her behind one of the book cases, Dean latches onto her neck.

“Dean…” She balls up her fist, not knowing what to do with her hands.

As Dean continues to suck a hickey onto her neck, he slaps both of his hands down onto her ass. When Dean pulls back, he glances down at her fists that are on her thighs.

“You could’ve stopped that, but didn’t. How bad do you really wanna win this?” After kissing her on the lips, Dean heads back to join Pat. Leaving (Y/N) standing there, wondering that herself.

 

“I quit.”

Dean turns his car back off, opening his door. “Quit what?”

“This game. I can’t do it anymore.” (Y/N) tells him with crossed arms.

“Okay.” As he’s closing his door back, she stops him.

“Okay? That’s it?”

“What do you want me to do?” He stares at her, one leg out of the car.

“I just thought I’d get more than an, “okay”.”

Getting fully out of his car, Dean throws his jacket and flannel in the front seat. Opening the trunk of his Impala, he shifts some things around, getting out a towel. Dean opens the backdoor and lays the towel out in the backseat.

“Lay on your back.”

“Um, here. We’re gonna…” (Y/N) looks between the backseat and Dean’s straight face.

“If you don’t want to that’s up to you. Your choice.” He leans against the car with his arms crossed. As he shrugs and goes to put the towel back, she says,

“Don’t.”

“Why shouldn’t I now?” Dean takes the two steps to get to her. “You want more than an, “okay” and I’ll happily give you one. But now I don’t want you to lay down.” Spinning them, Dean puts her up against the car.

She stands there with her arms on the top of the car, gasping as Dean yanks down her panties and leggings in one go.

Hands slowly trailing up her body, Dean presses himself up against her. “If someone were to walk or drive by, all they have to do is glance over here. See you bein’ fucked against my car…” Dean unbuckles his belt and pants. Semi erect, it doesn’t take him long to get hard.

He tugs her hips towards him, spreading her legs as far as they’ll go with the leggings on.

“But you like that, don’t you? Haven’t had my dick in a week and a half and you were wet when I put the towel down.” Dean eases in and wraps an arm around her waist. “If you would’ve quit earlier, I could’ve fucked you against your bookcase. To tell you the truth, I wanted to fuck you on my counter earlier. Picturin’ you in my apron, bent over, ready to take my cock.”

He slides a hand up around her neck. With each deep sharp thrust, Dean can feel her breath catch in her throat. Taking her hand, she places it on the one around her neck and tightens it. Dean brings her head back, making it almost touch his shoulder.

“You want Daddy to be rough with you.”

“Yes, Sir.” She pants.

Ripping her off the car, Dean pins her arms behind her and shoves her head into the backseat. Landing a stinging slap on the side of her ass, (Y/N) moans and cries are muffled by the seat.

Dean slows down his thrusts as she cums, thinking she was going to be released after she came back down, she clears her throat to say something.

He smirks as she shouts his name, when he picks up speed again.

Dean releases her arms, placing his hands on her hips.

Her hands find his wrists and she squeezes them.

Getting closer, Dean bites his lip to hold on just a little bit longer. (Y/N)’s legs go weak as she squirts on his dick. Pulling out, Dean gently moves her to get the towel, four swipes on his slit and he cums. Cock put away, he crouches, cleaning up her legs.

“You did good, Babe.” Dean praises, pulling her leggings back up.

Instead of her saying something, he hears a huff as a reply.

When he straightens back up, she lays her head under his chin.

“That got a little bit messier than I thought it would.” Dean tosses the towel on the floor of the car, kissing the top of her head.

“Can you come over tonight?” (Y/N) asks softly.

“Yeah, I can come over. I’m gonna go home, take a shower, and get some clothes. Then I’ll be over.”

Lifting her head for a kiss, Dean makes sure it’s soft and sweet.

When she pulls back, Dean kisses her forehead. “Try not to go to sleep without me.” He winks as she giggles headed to her car.

“I’ll try.”

While she gets into her car, Dean looks down the front of his jeans; one hundred percent satisfied with himself.

Their little game was absolutely worth it; in Dean’s opinion. They should do it again.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	10. Chapter 10

This is the first time neither of them actually has to go to either of their shops. Dean hired a baker, so he doesn’t have to go in every morning to prep his food. (Y/N) hired her first worker and this is the first time she’s leaving him alone in the shop.

Thus, they spent the night together and of course that lead them to various places in her apartment.

There’s a little problem this morning, Dean’s awake and currently hard, but (Y/N)’s still sleep. He doesn’t want her to feel left out. What kind of boyfriend would he be if he left her out?

Since she sleeps kind of wild, some of the cover was already off of her. He slowly pulls at the rest and the only movement from her is her right leg moving closer to him.

He ditches the cover on the floor and moves himself to between her legs.

Dipping his head down, he gives her clit a few light licks.

Her fingers twitch.

Continuing his actions, Dean moves his tongue in and out of her. He hears a moan and feels her getting wetter the longer he does so.

(Y/N)’s breathing changes as she starts to moan more and more. Finally, she opens her eyes and sees Dean looking back at her sucking on her clit. She gives him a sleepy smile, putting a hand on his head. He sticks two fingers in her pussy, retracting them using what’s on his fingers for the tip of his dick.

He places a hand on her hips as she grinds down on his tongue.

His hair is gripped and she pulls on it twice telling him to come up. Dean makes a trail with his lips and tongue up her stomach, makes a pit stop at breast, and arrives at her mouth. She flips them, straddling his hips. Placing a hand on his chest, the other directs his dick inside her.

Dean lets her take control of how fast and deep she goes, sucking and squeezing her breast. Her eyes are closed and her mouth is open from breathy moans. She switches her position for a bouncing motion rather than a forward and back one.

He rubs her clit in a circle, lightly pressing down. Her nails dig into his chest as she bites her lip and her brow furrows.

Before, (Y/N) had a bedframe without the headboard, but the other day she got a new one and this one has one. It was hitting the wall and she puts her hands on top of it, reducing the noise.

Dean shifts down the bed, keeping her leant forward he thrusts upwards. One of her hands snap down to a pillow.

She cums and Dean fucks her through it.

The headboard goes forgotten as Dean wraps his arms around her back. It’s around nine in the morning and her breathy moans are all gone. Dean groans at the sound of the headboard and her loud moans.

(Y/N) grinds down and whines as she cums again. Dick slipping out, Dean cums holding her tightly.

They don’t move aside from sharing lazy kisses, until there’s a knock at the door.

“Want me to get it?” Dean asks hands caressing her ass.

“Yes, please.”

He gets out of the bed and walks naked into the living room, picking up his shirt they discarded on the floor he wipes some cum off of himself. Dean opens the door after he put on the equally discarded underwear.

“Mornin’, how can I help you?” He asks voice sounding as if he just woke up.

The woman at the door turns red, looking him up and down. She tucks some dyed blue hair behind her ear, clearing her throat.

“Sorry, I was just wondering if everything’s okay. I just heard a lot of banging that I usually don’t.”

Dean licks his lips not able to stop his smirk. “Everything’s fine, thanks. We were, uh, I guess I could say, testin’ out her new frame.”

Her head quirks, before her face gets even redder. “Oh, I’m so sorry for interrupting.”

“You didn’t interrupt nothin’. We’re done for now. Is there anything else I could help you with?” Dean smiles at her, leaning on the doorframe.

“Um, is there anyway you guys can keep it from hitting t-the wall so hard?”

“I’ll figure out somethin’. We can test some things out, see what works best. Have a nice day and if we’re too loud again, just come right on over and knock.”

“Yeah, you too. I-I mean about the nice day not the loud- Nevermind, have a nice day.” She quickly walks away and Dean lets out a full belly laugh before he can close the door.

He’s such a dick.

“Who was it?” (Y/N) asks from the bathroom.

“It was your neighbor. She didn’t know what to think hearin’ the headboard.” He says, taking the underwear back off.

“She heard us?” (Y/N) asks, looking a little embarrassed.

“She didn’t hear you, she heard the headboard.” He’s staring at her bend over the bathtub, turning the water on for the shower.

“What did she think was happening?”

“I don’t know. I told her we were testin’ out your headboard.”

She sighs. “I won’t be able to look at her.”

“Why not?”

“Because she heard us having sex, Dean.”

“You can look at it as, at least you have a dick to ride.” He can’t help but find it cute when she looks at him shyly.

It doesn’t happen much, but when her shyness does come out, Dean gets a warm feeling inside knowing he can say things that can get that type of reaction.

She puts her hand under the stream, stepping into the shower. Sticking her hand out, he takes it and is dragged in with her.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	11. Chapter 11

"Whatcha doin' today?" Dean asks walking out of the mall.

"Uh, I'm just gonna be in the shop organizing things in the back room and my parents are taking me out later." (Y/N) says on the other end of the line.

"Alright, just get with me when ya can."

"Bye."

"B-ye."

She hung up before he could even say it. (Y/N) sounded extremely disappointed and Dean is getting into his car with a huge smirk on his face

Today's her birthday and she's thinking that he doesn't know that. Of course, he knows her birthday. This whole time he hasn't given any acknowledgement to that fact. He should feel bad, but he doesn't. Dean has to tease her a little.

So, with that being said, he's going to check on his own shop and then head over to hers.

 

After folding up the little bag he got from the mall, Dean slides it into the arm of his jacket, closing his car door.

As he enters his shop he greets his customers and both of his workers.

He grabs a cup, making the drink (Y/N) likes.

Chatting for a bit with both workers so he doesn't seem rude, he then heads over to her shop.

"How's it goin'?" Dean asks Tristen, who's standing at (Y/N)'s front counter.

"Good. How are you?"

"I'm just fine, thanks."

He nods, going back to his phone.

Dean moves around the counter with her drink. Coming around the doorframe, he sees (Y/N) standing at the biggest table rubber banding books.

"Hey, Babe."

"Hey, Dean."

His smirk gets a little bigger. "I got your drink."

She doesn't even turn around. "Thanks."

Dean sets the drink down, wrapping his arms around her waist.

"Dean, I'm really busy right now."

"Take a break." He says, leaving kisses on her neck.

"I'd rather not." She sighs, annoyed, as he stays kissing random spots on her neck.

"Why not?"

"Because I'm busy, Dean."

He finally gets off of her. "Fine, I'll leave you alone." Digging into his jacket sleeve, he brings out the folded bag he had, setting it down directly in front of her. "Bye." Dean doesn't wait as she opens it.

Out the door and down the sidewalk about to turn the corner to the parking lot, he hears feet hitting the pavement of the sidewalk. Dean glances behind himself to see (Y/N) with a huge smile on her face.

He stops and prepares for impact. Sure enough, her arms wrap around his waist from behind. Dean pulls her around to the front of himself.

(Y/N)'s squeezing him tight. "Thank you."

"You really thought I didn't know your birthday?"

"Yeah." She states shyly.

"Baby, you gotta give me more credit than that."

"Sorry."

Dean dips his head down, giving her a birthday kiss. When he pulls back, she has awe written across her face. He slides his hands into the back pockets of her jeans.

"After you're done with your parents, come over to my place. Bring some clothes so you can spend the night."

(Y/N) nods against his chest.

"Look at me."

She raises her head, giving him her undivided attention.

"I want you to wear what's in that bag."

As the image seems to pop up in her head, he can see excitement in her eyes.

Dean puts a hand on her jaw, closing the distance between them once again.

"Bring your collar." He whispers, against her lips.

"Yes, Sir."

Releasing her with a kiss to her temple, Dean says his farewell.

 

Dean's sprinkling red rose petals across his bed and his bedroom floor. He's already set up the candles. When he moved into his house the bedroom already had a light dimmer. He fiddles with it, finding the right setting.

Finished in his room, Dean heads out into his kitchen.

Grabbing two wine classes and the red wine he bought earlier, he sets them on the coffee table.

That’s everything. Only thing that’s missing is the birthday girl.

She texted him after she was done having dinner with her parents. So, she should be here in a little bit.

As if sensing Dean patiently waiting, a knock sounds off on his front door.

“Hey, Birthday Girl.”

“Hey.” She says smiling after a welcoming kiss, stepping into the house.

Dean takes off her backpack, placing it beside the couch. Taking her hand, he sits with her on the sofa.

“I didn’t know you drunk wine.”

He smirks. “On a normal day, I don’t. But it’s not a normal day.” Dean hands her the glass he just poured.

“Thank you.”

“Mhm.”

After pouring his own, Dean relaxes with his arm thrown on the back of the couch.

While they’re talking he notices she’s more giddy than usual when they drink together.

“What else did you drink today?”

She smiles against the rim of the glass. Dean slowly lowers her glass away from her lips.

“My friends wanted to take me out tonight, but I couldn’t. So, we just settled for some shots before I left to come over here. And I had two or three glasses of wine with my parents. Everything is coming together right now.”

“I see.” Dean sets his glass down.

As he gently takes hers away, she places her hands in her lap.

“You’ve had enough alcohol today.”

“But it’s my birthday…”

Dean chuckles. “I know. You’ll thank me later.” She was already on her second glass.

When he looks at her, she starts giggling.

“What’s so funny?”

“I just got fuckin’ butterflies when you looked at me.” (Y/N) places a hand on his face.

“Am I makin’ you nervous?”

She shakes her head. “Happy. You make me happy.” Her hand slides to his shoulder, playing with the collar of his t-shirt. “And you’re amazing and respectful.” Dean watches as she moves to settle herself over him. “And I like you, a lot.”

“I like you a lot too, Baby.” Dean says with his hands on her hips.

(Y/N) leans forward, connecting their foreheads. “It’s been a great birthday so far.”

“Hopefully, I can make it even better for you.”

“It can get better than this?” She asks with a slight grin.

Dean huffs. “You can find out.”

Sliding her hand to his jaw, (Y/N) brings him into a sweet kiss.

Biting and nipping at each other’s lips, Dean pulls back, licking his.

“You bring your collar for me?”

“Yes, Sir. And I’m wearing what you wanted me to.” She goes to unzip her jacket, but Dean stops her.

“How about you go in the room and get comfortable.” It wasn’t a suggestion.

Knowing that, she bites her lip, climbing out of his lap and walks to his bedroom.

When she makes it into the room, he hears her gasp.

Dean takes care of the wine before he goes into her bag. He finds the collar right on top.

Entering the room, (Y/N) stands with a candle up to her nose and a rose petal in her fingertips. She had on the black, see through mesh lingerie he bought her.

“Gimme that and lay down for me.”

She hands over the candle, smiling down at the petals crushing under her feet.

Dean grabs the lighter he had and makes his way around the room, lighting all the candles he placed. After he’s finished, he slides off his shirt and grabs the collar. He kneels onto the bed, pulling her up.

“You almost made me cry when I came in here.” She quietly confesses as he puts on her collar.

“Then I plan on makin’ it up to you.” Her hand goes up to the collar after he puts it on her. “Is it too tight?”

“No, Sir… Can you put it on the next hole?”

Dean smirks, pulling it tighter. He kisses just under her ear as he reaches under one of his pillows.

(Y/N) excitedly watches as he pulls both of her arms above her head, putting her in handcuffs.

“I think I just found out...” She whispers beneath him.

He chuckles, completing what he was doing.

Wasting no more time, Dean captures her lips, feeling the mesh fabric under his fingertips.

(Y/N) seems to realize, she can’t bring her arms around his neck.

“Just relax for me, Baby.” He whispers against her skin.

Dean moves the flimsy fabric away from her breasts. He gives each side attention until both nipples are erect. Grabbing the clamps connected to the collar, he puts them in their desired places.

Hearing her moan, he slowly makes his way down her body. Dean puts his mouth on her clothed pussy, teasing her through it. (Y/N) begins to grind against his mouth, craving direct attention to her clit. Holding her hips in place and looking at her, she gets the message to stop moving.

He teases her a little longer, smirking when he hears her whine.

“Tell me what you want, Baby.”

“I want you to put your mouth on me.”

“On your pussy?”

“Yes, Sir.” She tries to move her arms, forgetting they're locked in place.

Dean hooks his fingers under the fabric of the underwear, sliding it from under her ass and down her legs. She watches as he spreads her legs and puts them over his shoulders.

He nips on both of her thighs, slowly inching his way to her pussy. The contact she wants is finally made as Dean closes his eyes, focused on the noises she makes. She begins to grind again and he holds her in place once again.

“You can't wait to cum on my tongue, huh?” He sucks her clit.

“No, Sir.”

“You tryna rush through this?” Dean slides his tongue inside her pussy.

“No, Sir.” She buries her face in her arm.

“That’s what it seems like.” He moves up, her legs going with him. With a firm grip on her jaw, he whips her head around to face him. “You do it again, you won't be gettin’ what you really want tonight.”

His forceful tone makes her heartbeat a little faster and her arousal grow stronger. “Yes, Daddy.”

Dean sinks back down, holding her legs against her torso. Bent and restrained, all she can do is speak, but she's barely got ahold of that.

He shoves two fingers in her soaked hole and sucks and nips at her clit.

“Fuckfuckfuck. Mmm. I can't, I can’t. Daddy, please.”

Dean bites the underside of her thigh, causing her to gasp.

“What are you askin’ for?”

“I wanna move.”

“You askin’ me for permission?”

“Yes, Sir.”

Dean kisses her swollen clit. “Daddy doesn't want you to move right now.”

“Please.”

He separates her legs to look at her. “No.”

She bites her lip, gripping her hair. Returning to her pussy, he gets back to work. Dean let her go for a second and she began her grinding again.

“What did I say?” Dean barks, giving her ass a hard slap.

“Not to move.”

“And what did you do?” He slaps the same spot.

“I moved.”

Dean moves to the side of her and grabs ahold of her legs. “You wanna be hardheaded tonight.” An even harder slap lands on her right cheek.

“No, Sir. I'm sorry.” She cries preparing for the next hit.

Each smack she takes, she cries out in a mix of pleasure and pain.

Dean releases her legs, grabbing her face. “You better start listenin’.” He commands lowly.

“Yes, Daddy.”

Getting off the bed, Dean begins to take off his pants. She licks her lips, seeing his cock spring free. Stroking his painfully hard cock, he returns to his original spot between her legs.

She cums forcefully, pulling at her restraints.

Dean moves the mesh top over her head. Taking the clamps off her nipples, she sleepily watches him give each one special attention. Then he slides his cock inside of her.

(Y/N) buries her face in her arm as best as she can. Her voice is already wrecked because she was yelling during her punishment.

Thrusting sharply, deep inside of her, Dean sucks a hickey on her neck.

“You okay, Baby?”

All she can do is nod and moan.

Suddenly there's a sniff. Dean slows his thrusts, hearing it again. Gently, he turns her head. Her eyes are watered and a tear streak is going down the side of her face.

“Am I hurtin’ you?” He stops all together.

“No, keep going, please.” She wipes her face on arm. “I promise.”

Dean starts out slow, weary of the pace he had previously. Assured she was telling the truth, he goes back to the sharp thrusts.

Feeling himself get close, he slows down.

“You want me to cum in you?”

“Yes, Sir.” She says quietly, clearing her throat.

He speeds up again, capturing her lips. When she has to pull away all he hears are curse words in his ear.

Together they're reaching orgasm and just before she cums, she quietly cries, “I love you so fuckin’ much.”

Dean does one last thrust before he's cumming inside her. He pulls out slowly and goes straight for her restraints. Untying where the handcuffs were secured, he reaches into the nightstand and grabs the key to them.

He massages her arms a little since they were in one position the whole time.

“Sit up for me.” She does so, leaning against him.

Dean takes off her collar, rubbing the mark it left.

“Don't fall asleep on me yet. Go to the bathroom, Baby.” He doesn't think she's emptied any bit of that alcohol out her system other than sweat.

When she sways back towards the pillows, Dean gets off the bed and tugs her up.

She’s unsteady on her feet.

After helping her to the bathroom, he returns to flick the petals off the cover. Some were attached to their skin mainly hers, but Dean got them off. He's tired also, but he has to take care of her first.

When she comes back in, instead of going for the bed, she latches onto Dean as he’s blowing out candles.

“Thank you, Dean.” She says in her almost fully gone voice.

“Anything for my girl.” He kisses her forehead. “Let's get you in bed.” Directing her into bed, he covers her up.

Dean blows the rest of the candles out and turns the light completely off. Getting in the bed, he doesn't get the chance to properly cover himself up yet because she rolls and scoots over, burying her face in his chest. He smiles softly, correcting the cover around them.

She’s asleep in no time. He kisses the top of her head and brings her closer with an arm around her.

He’ll run her a bath in the morning.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	12. Chapter 12

“That doesn’t go there.” (Y/N) exclaims.

“Show me where it goes then.” Dean pushes the instruction booklet towards her.

She takes it in hand, fully sure of herself. “It goes… uh…”

He was building her a TV stand. There was a board that wasn’t labeled with a letter. Dean knows what he’s doing is right, she’s been over his shoulder telling him he’s doing wrong since he started.

“That’s what I thought.” He takes back the booklet.

As he screws the board in place, she’s staring at him seemingly annoyed.

“Problem?”

“Why do you have an attitude?”

“Who has an attitude?” Dean counters looking at the next step.

“You do.” (Y/N) gets up, heading to the kitchen.

“Why shouldn’t I have an attitude?”

“Because I’m just trying to fuckin’ help you out.”

Dean gets together the next pieces he needs. “You’ve been over my motherfuckin’ shoulder since I started. I can read the directions. If I needed your help, I would ask for it. You asked me to put this damn thing together. Chill out.”

His jaw flexes as he puts the next board on.

“Still have a fucking attitude.” (Y/N) mumbles, biting the skin on her thumb.

Dean straightens up. “Come here.” He says coolly.

She freezes for a second, hearing the real tone that was underneath the cool one.

“Come here.”

(Y/N) looks at the floor, hesitating. She doesn’t walk to Dean, she heads down the hall to her bedroom. When she hears him get up, she speeds up.

Dean finds her attempting to fold up clothes she had on her bed.

“What’s up with you?”

“Nothing’s up with me.” She says, putting a folded shirt aside. Her tone still the same.

He grabs her arm, turning her around. “You’ve been given me a lot of lip recently.”

“…No, I haven’t…”

“You don’t think you have?” Dean tightens his grip.

“You’ve been having a rude ass attitude.”

“How so?”

She looks away like the answer is floating in the air. “I-I don’t think I need to tell you.”

Dean backs her into a clear space on the wall they were standing by. “You’re actin’ out.”

(Y/N) looks down at his chest, shaking her head.

Swiftly, he turns her around, holding her against the wall. Dean pins her in place with his body.

“I’ve been busy lately. Haven’t had the time to come over here and spend some time with you.” Dean puts his hand on her waist. “But I don’t think that warrants you given me lip when I’m on the phone with you.”

“I-I haven’t been giving you lip.”

“Remember the last time we had to deal with you givin’ me attitude?”

Her gulp is audible. “Yes, Sir.”

“I’m thinkin’ I let you off easy. What about you?”

She stays quiet.

“Oh, you don’t wanna give me no lip now?”

“No, Sir.”

Dean removes himself, pushing her back into the wall when she tries to get off of it.

“I won’t give you anymore lip. I’m sorry, Sir.” She quickly says, hearing his belt buckle.

“Does three days sound like a long time to you?”

He can tell the question confuses her. “Um, no?”

“What about a week?” Dean pulls her off the wall.

“For what?”

“Just answer the question, (Y/N).” He holds her hands behind her back.

“No?”

Dean pushes her into her clothes, holding her there.

“Since three days to a week isn’t long, you won’t be cummin’ for a week in a half.”

“NO! I’m sorry, three days is enough.”

“It’s too late now.”

“Fuck.” She whispers into a towel.

Dean knows she does this stuff on purpose because she doesn’t want to flat out ask for him to be rough with her. Sometimes, she’s shy about starting things up on any other day also. But since she does it on purpose, he likes to think of things that’ll make her think about doing things on purpose in the future. Whether she decides to keep doing it, he doesn’t know.

It's sort of interesting how when they’re relationship first started she was mouthy, but now she doesn't call Dean her “manly bitch”. As the relationship progresses, she allows herself to become more and more vulnerable. He loves the fact that she trusts him enough with this whole ordeal that is their sex life. Even when Dean isn't choking, spanking, or cuffing her, they still have this trust in their relationship.

Dean releases her hands, snatching down the shorts she had on.

“Remember when I told you that we had to practice keepin’ you quiet?”

“…No,Sir…”

Dean flips her onto her back. “So now you wanna lie?”

She's biting her lip as she stares at him weighing her options on telling the truth. “I remember.” She says quietly, slightly ashamed that she lied.

Dean stares at her, face neutral. “Wow, you're really on a fuckin’ roll.”

(Y/N) gets rid of her shorts, flipping back on her stomach with her bare ass up in the air.

“I should spank you for it?”

“Yes,Sir.” She pushes her ass back into his hand when she feels it hovering.

“Why?”

“Because I just lied to you.”

The first smack catches her off guard. She puts a hand over her mouth to keep herself quiet. When he's done, she keeps her eyes closed, blowing out a breath. Dean unzips his pants, takes out his hard cock, and makes her arch her back some more before inserting himself into her moist pussy.

Her fight to stay quiet is a tough one. Dean can hear the little whines and whimpers she makes because she’s not allowed to be loud. He's not making it any easier hitting her g-spot every other time. She finally breaks when he slams her back down on his dick.

“Daddy, I need to cum.” She cries about to rip her sheet off the bed.

“What did I say?”

“That I can't.” The only thing that's holding her up is Dean. “Please, I'm sorry.” Her toes are curled as if she’s doing everything she can not to disobey orders.

“Well, you should've thought about that before you wanted to lie and give me lip. You got a lesson to learn, you understand me?”

“Yes, Daddy.” She whines.

Taking aim for her weak spot, Dean slams into it repeatedly. (Y/N) hits the bed with her palm, shaking with the need to release.

Feeling her getting ready to cum, he pulls out. Pulling her off the bed, he makes her get on her knees, resting the tip of his cock on her lips.

“Ah.” He says when she reaches for her pussy.

As she sucks on his tip, Dean pumps his own shaft ready for release. He cums into her mouth and she sits there, waiting for him to finish.

“Open.” He says swiping up some cum that escaped.

(Y/N) opens her mouth for Dean to put the swiped up cum inside with rest.

“Swallow.”

She does as she's told.

After tucking himself back he pulls her up, tilting her head up so she'll look at him.

“I’m about to finish what I was doin’ and I don't want you over my shoulder tellin’ me what to do.”

“Yes, Sir.” She says meekly.

Dean gives her a peck on the lips before walking out of the room.

Situating himself back on the floor, he picks up where he left off. (Y/N) quietly comes out of her room. Dean hears her open the fridge, digging around in it. She walks into the living room, placing an opened beer in front of him and taking away the empty one.

He smirks to himself, not stopping the flow of his work. When she settles down beside him, she plays with one of the nails that were in the pack.

They sit in semi silence while Dean finishes. He puts her to work passing him some of the items he needs. The stand looks perfect when he finishes if he says so himself.

Together they clear the space needed.

Getting everything on the new stand, Dean has her finish that up while he breakdown the old one.

Coming back from throwing away all the broke down pieces, he finds her sitting on the couch waiting for him.

He has her pick a movie she wants to watch. Dean grabs the cover that was over the back of the couch, throwing it over the both them as she uses him as a body pillow.

They both wind up taking a nap, leaving the movie unfinished.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	13. Chapter 13

It’s been a week in a half and (Y/N) has been behaving herself. Dean's made sure she's kept to her punishment. 

So, today was the day he was going to let her cum. But he was going to draw it out with the little helper he bought. 

He was on his way over to her place, ready to give her what she's been looking forward to. 

Car parked and bag taken out, he heads to her apartment. He opens the door having her unlock it beforehand. She's laying on the couch covered up like she's cold. 

“Hey, Baby.” 

“Hey.” She gets up and puts her arms under his open flannel. She only had on her collar, bra, and panties. 

Dean smiles as he kisses the top of her head. “I got somethin’ for you.” 

“What is it?” She asks quietly. 

“You’ll find out.” Taking her hand, he directs her to the bedroom. 

He makes her lay down as he gets the box out of the bag. 

“You’ve been on punishment for how long?” 

“Week in a half.” She replies staring at the box he was opening. 

“Why was that?” 

“Because I was being mouthy.” 

“Right. Are you gonna get mouthy with me again?” He opens the pack of batteries he bought. 

“No, Sir.” 

“You're not just sayin’ that?” 

“No, Sir.” 

He looks at where she's laying. “Good girl.” 

(Y/N) smiles shyly, messing with her collar. He just realized that's a different one. It doesn't have nipple clamps on it and it's red while her other is black. 

“You like wearin’ collars?” 

“Mhm.” Dean quirks his brow. “Yes, Sir.” 

“Why's that?” 

By the look on her face, she seems embarrassed to say. 

“You like the thought of somebody ownin’ you?” 

She slowly nods. He’s not going to make her voice it. Dean knew it wasn't only because she liked the feeling of being choked. 

Finished with what he was doing, he turns the vibrator on, feeling the different settings against his hand. He needs a towel. 

After having her get a towel he makes her place it under her ass and thighs. 

Her panties are already wet when he starts pulling them off. He also removes her bra before things get started. 

“Relax. You worked hard for today.” Dean says after kissing her. 

She rests her head against her pillow. 

Placing the start of the wand on pussy, he turns it on. She bites her lip and starts playing with her breasts. 

“Feel good, Baby?” 

“Yes, Sir.” She moans. 

“Good, ‘cause you're not comin’ until I say you can cum.” 

She stops playing with her tits. Not only does she have to wait to cum, Dean turns the speed up on the wand. 

(Y/N) draws her legs up, they’re snatched back down. 

“You either keep ‘em down or I'll do it for you.” 

“Yes, Sir.” She whines. Right after saying this they go back up again. 

Dean snatches them down once again. He spreads them and uses his forearms to keep them down. 

(Y/N) places a hand on his wrist, trying to pull the toy away. 

“Ya know what?” Dean turns it off. 

She watches him climb up the bed beside her. 

“Come here.” 

(Y/N) places herself on his lap where he directed her. 

“Try somethin’ else.” He mumbles to himself. 

She lays her head on his shoulder, thinking she's scott free. Dean wraps his arm around her back placing his hand on the arm that wasn't already pinned down. When he grabs the toy, she squeezes her thighs together. 

“Open ‘em or you won't be cummin’ today.” 

(Y/N) opens them a little, but Dean's able to shove the wand where he needs it to be. 

“You didn't think I was lettin’ you off easy, did ya? Ah, you grab it again, I'm turnin’ it up.” 

She directs her hand to his shirt. 

“Daddy, stop.” She cries, after a while of not being able to keep still. 

“Why?” He pulls his head back to look at her. 

“‘Cause I'm gonna cum.” She moved her hand to his neck. 

Dean smirks as she closes her eyes, trying her hardest not to. 

“You cummin’ on my lap?” She looks at him, not knowing how to respond. Dean kisses her forehead, keeping his lips there. “Cum for me, Baby.” He starts moving the wand in a circular motion. “I know you feel my dick against your ass. You keep bein’ a good girl you can have it.” 

Her hand tightens and she moans loudly as she cums hard. Dean keeps the toy where she has it trapped between her legs and his pants become wet. He waits for her to finish and she whines for him take it off her sensitive clit. 

“Good job, Princess. You got Papa all wet.” Dropping his hand between her legs, he slips two fingers in her pussy, admiring how wet she is. 

“Can I have your cock now, Mr. Winchester?” She asks meekly, testing the new name out. 

“You know how to get it.” He takes his fingers away. 

Slipping off his lap, she unzips him and quietly asks him to pull his pants off. 

Back against the headboard, (Y/N) settles between his legs. She takes his hard cock in hand and her mouth follows right after. 

When she goes down, Dean holds her there. 

“When I move my hand, I want you to climb on my dick, understand me?” 

He feels her throat vibrate and her gag reflex gets going. Dean pulls off by the hair, satisfied with how wrecked she looks. 

When she's released, she immediately does what she was told. 

“Start bouncin’.” 

(Y/N) places her hands on his shoulders, following orders. 

“Who's pussy is this?” Dean asks teasing her clit as she bounces. 

“Yours, Mr. Winchester.” She moans looking down at his thumb on her clit. 

“Who do you belong to?” 

“You, Daddy.” (Y/N)’s thighs are starting to shake. 

She leans into him, stopping. 

“I need to take over?” 

Feeling her nod against his neck, he lays her back and places the towel under her again. 

“You tired, Princess?” 

“Yes, sir.” 

Dean slides into her again. While she has her eyes closed, he reaches back for the toy. 

“Dean!” She yelps, hands shooting down to his wrist. 

He watches as she fights to keep her eyes from rolling back. It's not something she wins. Her cries of pleasure turn him on even more. 

Dean uses the wand for a little longer and tosses it to the side. Leaning over her, she wraps her arms around him as he pounds into her. With a hand pulling her hair and biting on her shoulder, (Y/N) digs her nails into his back; hard enough for him to feel it through two shirts. 

She cums before he does and it's a good thing the towel is there. Dean stays inside her while he cums and she moans at the fill of his load. 

When he pulls out, some of it drips onto the towel and he puts two fingers in scooping it out. Her mouth automatically opens when she sees them coming towards her. She sucks them clean, smiling at him. 

Dean kisses her roughly, hand going to her collar. He unsnaps it and pulls it off. 

“You see what happens when you're a good girl?” 

“Yes, Sir.” She says sleepily. 

He moves the side of the bed and she climbs in his lap, resting her head on his shoulder. 

“I'm not leavin’, Baby.” 

“Lay down.” She meekly demands. 

Dean removes his shirts after convincing her to lay down first. Bed cleared he lays his head on a pillow and she glues herself to his side. 

He covers them up and she basically falls asleep laying on top of him.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	14. Chapter 14

Dean was out having a coffee with his brother, they were laughing about a case Sam had a while ago when his phone rang. He ignored the first call because he was with his brother, but then the second call came. Flipping the phone over to see who it is, he just gets this sinking feeling something is wrong.

It's (Y/N), but she's been acting weird. He asked her if she was okay and she always says yes. It wasn't until after he cuffed her to his bed and used that magic wand on her. He kept her from cumming countless of times that evening and when she finally did; Dean had to go over his folks’ house. When he walked her to her car she was alright. The next day she called but he was so busy, he couldn't stay on the phone long.

He holds up a finger at Sam.

“Hey, (Y/N)."

“Hey.” She sounds small, almost fragile-like.

He presses on his other ear to be able to hear better. “What’s up?”

“I-I wanted to talk to you.”

“Sweetie, I'm with my brother right now.” Sam smirks at the nickname.

It's silent for a few seconds. “Sorry.”

Dean takes the phone off his ear. “Hold on, Sam.”

Sam nods, pulling out his own phone.

Walking outside, Dean walks a little bit away from the coffee shop.

“What's goin’ on?”

“Nothing. I can wait until you're done with your brother.”

“Why are you cryin’?”

“I'm not.” She lies.

“Where are you?”

“Sitting in my car at the store.”

“Which one?”

“Target.”

“You shop yet?”

“No.”

“Stay there.” He jogs back towards the coffee shop.

“Okay…”

Dean hangs up the phone, placing it in his pocket.

“Sam, I gotta go.” He snatches up his half empty coffee.

“What happened?” Sam springs up to, keeping up with his brother’s pace.

“That's what I’m tryna figure out.”

 

Dean pulls into the parking lot, searching for her car. He finally spots it, it's further back in the parking lot by itself.

Pulling up beside it, (Y/N) looks over at him. She looks so sad and her eyes are red.

He gets out the car and opens her door squatting.

“What's wrong, Baby?”

She wipes a hand up her nose. “I don't think we should do it anymore.”

“Do what?” He wipes a tear away.

“I shouldn't be wearing a collar and letting you choke me.”

“I thought you liked that.” Dean says confused.

“I do but it's not right.”

Dean frowns. “If you like it and you're not gettin’ hurt then I don't see the problem.”

“I had bruises on my wrists and neck, my mom saw them and thought you were beating me.”

“You know I would never do that.”

“I know. Even though it was embarrassing, I told her how I got them and she said that it wasn't right.” She wipes her face with her shirt.

“What do you think?”

“I don't know.” She mumbles not looking at him.

“You wanna stop?”

“No.”

“Problem solved.” He gets up.

About to kiss her goodbye, she pulls back. “Do you care about me?”

“What made you ask that?”

(Y/N) looks down at herself, not answering.

“‘Course I care about you, Princess.” Dean crouches beside her again. “Stop all that cryin’.” He says softly. “Is this about the other night when I had go to my parents’ house?”

She nods slightly.

He will admit after they finished, he rushed her out the door too quickly. They'll go to sleep or he'll spend type of time with her. But he had to go and since then he’s been too busy to make up for that time.

“I'm sorry, I got busy, Baby. I promise I wasn't tryna ignore you or anything like that. Forgive me?”

(Y/N) stays quiet, shyly gazing at him.

“If you don't, I understand. You don't have to lie.”

“You could’ve called me.” She states weakly.

“I know, I wasn't thinkin’.” Dean looks around the parking lot. “Can I make it up to you?”

“Yes.”

“Can I do it right now?”

“…Yes…”

“Hold on.” Dean leaves her door open and slips into his car.

He parks his car closer and a little crooked. Dean opens his car door, making sure not to scratch the paint on her car.

This time Dean gets on his knees. He helps her maneuver out of the jeggings she had on. Asking her to lean back and scoot forward, Dean spreads her legs.

He looks at her face before sticking his tongue inside her. Dean puts her thighs over his shoulders.

Feeling her hand on top of his head, he allows her to grind on his face.

Dean roughly licks her clit as she suppresses her moans.

As he fucks her with his tongue once again, (Y/N) is trying to keep from gripping his hair.

“Pull it, Baby.” He feels her latch on.

“Dean, you don't have to do this.”

“You want me to stop?”

“No.” She says far too quickly.

He hums against her pussy.

Suddenly he feels her hands on the sides of his head. Looking at her, she wants him to sit up. Dean's slides her thighs off his shoulders and goes into the kiss she was wanting; after wiping his face with his shirt. Sticking his fingers in her pussy and rubbing her clit with his thumb, she begins to grind on his hand.

“I'm sorry.” He whispers between them.

Her half-closed eyes roam his face, she smiles closing her eyes, forehead falling onto his.

“Can you call me a good girl?” She asks timidly.

Dean smiles. “You’re my good girl. My pretty little good girl. You’ll always be my good girl, right?”

“Yes, Mr. Winchester.” She moans.

She's getting closer and closer to cumming.

“And I'll always be your what?”

“My Daddy.” She says with a cute little smile.

“You gonna cum for Daddy?”

(Y/N) opens her eyes, hands holding tightly onto his shoulders. Her brow keeps quivering and she starts to breath faster than she was.

“That’s it, cum for Daddy. You can do it, Babygirl.”

One rough rub on her clit has her cumming. She stares at him as she does so and Dean grins back.

When she's done shaking, he slides his fingers out, licking the wetness that was on them.

“Give me your panties.” She reaches in the passenger seat.

Dean takes them and wipes off his hand before cleaning the cum that was on her and the little bit that got on the seat.

He holds his hand out for her pants.

“Now, what we’re gonna do is move our cars closer and go shoppin’ like you wanted to.” He pulls her out the car, quickly pulling the jeggings over her bare ass.

“You're still…”

Dean looks down at the bulge in his pants. “After this goes down.”

She giggles, wrapping her arms around him.

“Thank you.”

Before he can respond, a cop car comes around. He parks in front of (Y/N)’s car and she worriedly looks up at Dean.

“What are you guys doing over here?” He asks through the rolled down window.

“My girlfriend had a breakdown, so we came over here to get that sorted out. Wanted to give her some privacy.”

The officer nods. “You okay, Ma’am?”

“Yes, Officer. Thank you.” She lays her head on Dean's chest.

Nodding once again the officer leaves.

Tilting her head up, Dean kisses her forehead. “Let's go.”

They find parking spots opposite of each other. Dean's out the car first, so he waits for (Y/N) at her trunk.

Lacing their fingers together they walk into the store.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	15. Chapter 15

Just coming back from dinner, Dean and (Y/N) were at his house. She was going to spend the night. 

The couple was lying on the couch, watching movies to wind down. Dean was drifting off. He had his arm wrapped around (Y/N)’s waist, eyes slowly creeping closed. 

Not knowing he drifted off, (Y/N) starts to subtly grind her ass on him. Trying to silently give him a hint. 

Feeling this, Dean frowns a little before he realizes what's going on. Eyes still closed, he nuzzles his face into her neck. 

“You horny, Baby?” He asks voice rough, clearing his throat after. 

“…Yeah…” 

“What do you want me to do?” Dean whispers before kissing her neck. 

She’s silent for a bit, messing with his fingers. “I don't know…” 

Slipping his hand out from under hers, Dean slides his hand into her panties. 

“Are you fine with a lazy day?” 

“Yes, Sir.” 

Dean’s hand is cuffed over her pussy. He moves his hand to her thigh, positioning it over his leg. 

Turning her head, she puckers up for a kiss. As they lip lock slowly, he puts his hand on the outside of her panties. Caressing her pussy through them. 

Moving his lips to her ear, he sucks and pulls at the lobe. Dean blindly finds her hand and slides it under her panties, making her rub her clit as he inserts his fingers inside her. 

(Y/N) moves as flat on her back as she can on the couch when he scoots as far back as he can. 

As they continue their actions, her eyes roam his face. Dean's dick is getting harder and harder the longer he feels the wetness from her pussy. 

She bites her lip, slowing down how fast she was rubbing her clit. 

Hand coming out of her panties, Dean places it on her hip, sliding it up slowly. They gaze at each other quietly. 

(Y/N) flips onto her side and throws her leg over Dean’s as he watches her hand move around down below. 

Licking his lips, he pulls his cock out of the pj’s he was going commando in. She immediately switches her attention to it. 

Pumping a few times, she watches precum ooze out his slit. Dean grabs her ass, giving it a hard squeeze before moving onto her panties and pulling them out the way of his dick’s destination. 

She kisses him as she penetrates herself with his cock. (Y/N) buries her face into his neck and Dean holds her close as he thrusts slowly and deeply inside of her. 

Her moans sound as if she's innocent. Like she doesn't wear collars or even like to be slapped around. Dean's enjoying this more than he thought he would. 

There's something fragile here. In the sense of her not calling him some dominating name or him having to control her. This is the kind of sex that reminds him that they're a couple. 

When you're a couple, certain feelings arise that you don't know how to deal with until the right moment. Or the moment you feel brave enough to cease it. (Y/N) did it on her birthday. But not knowing if it was just the alcohol, the literal heat of the moment, or both, Dean didn't want to act on it. 

As she moans his name softly into his skin, he gets this sudden feeling that her words that night were very much real. 

Dean slides out of her and puts her on her back. He hovers over her, rubbing his shaft along the outside of her pussy. She reaches down and directs it where she wants it. 

Lifting her shirt, he pulls on her nipples as she grips the armrest and the edge of one of the cushions. 

“Deeper…” She weakly commands, lost in the pleasure from his cock. 

“You want me to go deeper, Baby?” 

(Y/N) nods, biting her lip with glazed over eyes staring at him. 

Dean shoves his arms under her, wrapping them under her back. She spreads her legs wider, moaning crazily at his first buried thrust. 

Her hands move to the back of his shirt, balling it up to find a little bit of ground. 

Licking and sucking under her jawline, Dean moves on to trace the shell of her ear with his tongue. He's never done it before, but the action turns her on even more. 

“…Fuck…” She moans feeling him suck on the top of her ear. 

He feels her rubbing his back and balling up his shirt repeatedly as if she doesn't know what she wants to do just yet. Dean feels her walls pulsating around him. 

Finding her lips again, he stays deep inside her as he kisses her passionately. 

Keeping their foreheads connected when Dean pulls back, he starts up his thrusts again; making them sharper than before. 

She bites her lip as her eyelids start fluttering. 

“You don't hafta hold on, Baby.” Dean whispers. 

“I'm waiting for you.” She pants back. 

“I'm not gonna make you wait long.” Pulling almost fully out, Dean slams back in. 

After doing it a few more times, (Y/N) can't hold on anymore. She cums pulling at his shirt and her head goes back into the couch. Dean fucks her through her orgasm. 

Keeping him over her, she smiles sweetly at him, allowing him to continue to fuck her wet pussy. 

Making him stay inside of her while she kisses him, Dean feels her begin to milk his cock. With the walls of her pussy pulsating around him, he cums deep inside her. She grinds on his cock, wanting every little bit of his cum. 

He thought it was going to be a lazy fuck, but he's still hard. 

Dean pulls out and watches as some of their combined cum spill out onto the couch. (Y/N)’s brows raise when she sees his cock still standing proud. 

Pulling his shirt off, he shoves his pj pants down about to wrap his hand around himself. (Y/N) stops him. She stares at his cock, watching a droplet of cum slide down his shaft. 

Dean pulls her in for a kiss. After she's done, she dips her head low, taking him into her mouth. She sits back swallowing the cum that she got from his shaft. 

Standing in front of him, (Y/N) slides her cum filled panties down. She climbs in his lap and begins riding him. 

Dean grips her ass, making her grind harder. 

“Love my cock, huh?” 

“Mhm.” She moans holding the back of the couch. “…Fuck me. I wanna cum again…” 

Dean makes her leans back onto the coffee table. He’s standing with his hands on her hips and his dick inside her again. 

“Oh!” She holds onto his wrists as he begins to fuck her. 

Her face is screwed up in pleasure as the table creaked underneath her. 

Moving a hand to her pussy, he flicks her clit. 

“Mmmm, pleasepleaseplease. Dean…” She cries squirming on the table. “Use me. Use me, Daddy.” 

Dean continues his actions, only using his thumb to rub her clit now. 

“You gonna fill me up again?” She asks with a filthy smile. 

“Yeah, I’m gonna fill you up, Baby.” 

(Y/N) lets out the most pornographic noise he has ever heard leave her mouth. His cock jumps inside her. 

“Fill me with with your cum, Daddy. I want it so bad.” 

Dean's staring at her, turned on by her words. Noticing this, she licks her lips lewdly. 

“Leave it deep inside me like you did before, Daddy.” 

He gets on his knees to continue fucking her. (Y/N)’s between wanting to talk and not wanting to cum just yet. But she feels it rushing up on her. 

“Da-Dean… you're fucking me so good, I don't know what to call you. Your dick is so good to me. You always fill me up with your big thick cock. I love it when you- ah- when you shove it i-inside me. When I have it… down my throat it's so big I can't breathe right.” 

Dean snatches her off the table into his lap, filling himself about to explode. 

“My pussy belongs to you and only you. You're fucking me so deep, I can feel you in my stomach.” She kisses him roughly. 

There a metallic taste in his mouth as she grinds down on his dick. Dean can feel her juices run down his dick as she squirts. Again, he fucks her through it. 

Holding Dean’s head in her hands, she pulls her head back to look him in the eyes. 

“Leave it deep inside me. I wanna feel it when I wake up.” 

“Fuckin’ filthy…” Dean whispers with a slight smirk. 

For a second he sees shyness in her eyes. She's never spoken like this to him before, at least not this long. 

“Tell me what else you want.” He’s almost right at the edge. 

“I want you to fuck me when we wake up. Hold me to the bed and choke me until I see stars. I don't want you to cum in me because I want to suck it from your dick and swallow every drop of cum you unload.” She moans at the thought, grinding down on him one last time. 

Dean cums hard inside of her just as deep as he did before. Like before she milks every bit she can, until Dean has to pull out. 

Sweaty, breathless, and feeling his hot cum drip out of her, Dean holds her and looks her into her half-closed eyes. 

“I love you.” 

She freezes, eyes darting between his. “Really?” The vulnerability of the question is shown all over her face. 

Dean’s not even finished nodding when she kisses him and buries her head in his neck. 

…He loves her…

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	16. Chapter 16

Dean decided to play another little game. It’s called, see how long she can last with a vibrator in her pussy until she begs for his cock. Long title, he knows.

So, right now they were in a sex shop looking for one.

(Y/N) picked one up, but Dean made her put it back because it was too small. She’s not getting off easy.

“Here.” Dean says, handing her an average dildo vibe. It was thick, but not too thick. Just thick enough to make her feel full.

They go to the register and (Y/N) shyly places it on the counter. After he pays for it, he hands off the bag to her, wrapping an arm around her waist.

On the drive to his house, he teases her with his hand between her legs. She’s staring out the window hand over her mouth.

“Slide down a little bit.” Dean commands at a stoplight.

When she does so, he slips a finger into her pussy feeling how wet she’s gotten since he’s started his teasing.

“You know I’m puttin’ that vibe in, right?”

“I… I thought I was gonna do it.” Her head falls back with a moan.

“There’s a certain way I want it in there and you’re not gonna touch it.”

“Yes, Sir.”

When the stoplight changes, he takes his finger back out returning to teasing her clit.

Arriving at his house, they get out and (Y/N) is glued to his side as he opens the door.

“Clothes off. Wait for me to come back.” He demands, taking off his jacket.

Dean goes into his room, opening a drawer in his nightstand. With the collar she left at his house the other day in hand, he exits and grabs a towel.

Coming back into the living room, (Y/N) is completely naked patiently waiting for him.

After he lays the towel down on the couch, he puts her collar on and has her lay on top of the towel.

Freeing the vibrator from its packaging, Dean goes in search for some batteries. Finding some in his closet he comes back inserting it into the vibe.

“Alright, Princess.”

(Y/N) perks up at the sound of his voice and readjusts herself on the couch.

Dean bends over the back of the couch and starts to gently rub her clit just to get her a little more wet. Slowly he inserts the vibe into her pussy.

(Y/N) grabs his forearm, moaning.

All the way in, Dean removes his fingers from her clit and looks her dead in the eyes as he turns the vibrator all the way up.

She’s so surprised, just an instant look of betrayal crosses her face.

“You didn’t say you’d turn it all the way up.”

“I didn’t say I’d turn it to be low either.” Dean quirks his brow. “Cross your legs.”

(Y/N) jerks a bit from the feeling of the vibe, doing what she’s told.

Dean lifts her legs and sits, placing them in his lap. He listens to the little moans that slip out of her.

“Daddy, I don’t… I don’t know if can do this...” She’s already breathing a little heavily.

“What are you thinkin’ about?” Dean questions coolly, gently running his hand on her shins.

“A-about your cock in me.” (Y/N) balls up her hands, head falling back on the arm rest.

“Yeah? What about my cock in you?”

“How it fills me up a-and how deep it goes inside me…”

Dean hums lightly with a huff. “Do you want me inside you?”

Gaping at him, (Y/N) stands her ground and shakes her head. “No, Sir.”

“Hm, good girl.”

Reaching for the remote, Dean turns on the TV. He sits and listens to (Y/N)’s moans, feeling her jerk a bit in his hold. After a little bit of time passing, Dean hears a familiar noise come out of her. It’s a noise where she’s trying not to cum, but ends up failing.

Looking at her, (Y/N) has a hand over her mouth, eyes squeezed shut. Dean waits for her to finish.

“I didn’t mean to.” She says right as she opens her eyes to see Dean staring at her.

“Hm. Baby, I don’t care that you came. Just don’t cover your mouth. You know I like to hear you.” Gently, he opens her legs.

The end of vibrator is covered in her juices along with the inside of her thighs. Slowly, he pulls the vibe out, smirking as she moans at the loss of it.

Cleaning it off with a bit of the towel, he leaves it there and goes back to watching TV.

“Is that it?”

His brow quirks. “What was that?”

“W-was that all we were going to do?” She asks fiddling with her collar.

“You already came, so you don’t need my cock now, do you?”

(Y/N) slightly squints at him. “I would l- No, I don’t.” She just realized what he was doing.

“Well, that answers that.” Dean moves her leg a little, unbuckling his belt, unbuttoning, and unzipping his jeans to pull his half hard cock out.

Moving a hand towards her, Dean sticks his fingers inside her, making sure they’re nice and wet before pulling them out and using it on himself.

As he strokes himself, he feels her eyes glued on him and his cock.

Making himself comfortable, Dean continues to tug on his cock. Out the corner of his eye, he notices she’s pouting. He rolls his head over to look at her.

Holding eye contact, he licks his lips and her eyes drop down to them before she quickly looks away. Grabbing her wrist, he uses it to pull her closer.

When she’s close enough, Dean roughly kisses her. (Y/N) moans, resting a hand on his thigh.

After Dean bites her lip, she pulls back to catch her breath. Snatching her up, Dean settles her over his cock, slowly sliding into her pussy.

(Y/N) bites her lip gripping his shoulders tightly, moaning from the instant fill of his dick.

With her fully seated on his cock, Dean notices a bit of a smile on her face.

“Happy that Daddy lost, huh?”

“Yes, Sir.” (Y/N) response shyly, wrapping her arms around his shoulders.

This is his first time ever losing one of their little games.

Dean grabs her hips moving her back and forth. (Y/N) moves forward to hold onto the back of the couch, beginning to bounce up and down.

Leaning his head back, he admires the view of her blissed out face and bouncing tits.

After a while, her movements begin to slow down. Wrapping his arms around her waist, Dean scoots down a little and starts thrusting into her.

Cumming for the second time but this time with a shout of his name, Dean feels himself close to his climax.

Just before he slides out of her, she grabs his face and crashes their lips together.

Feeling to the side of them, he grabs the towel sending the vibe to the floor. One stroke later, Dean cums into the towel.

(Y/N) slumps against him, nuzzling his neck.

“Why don’t you head to the room while I clean this up.” He says gently, rubbing her back.

Slowly, she removes herself from his warmth. As she leaves, Dean completely takes off his jeans. Straightening up everything and picking things up that doesn’t belong in the living room, he heads to his bedroom.

What he sees makes him smile softly.

(Y/N) already fell asleep waiting on him.

Putting things where they need to be, Dean sheds the rest of his clothes. Before he gets into bed, he leans over her and unbuckling her collar.

“Shh, it’s just me, baby. Go back to sleep.” Dean whispers as (Y/N) opens her eyes.

Placing the collar where he got it, Dean finally climbs into bed and pulls her close.

He never planned on winning the game today.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!!<3


End file.
